AU2008234152A1 - Insecticidal derivatives of substituted benzylamines - Google Patents

Description

WO 2008/119511 PCT/EP2008/002475 Insecticidal derivatives of substituted benzylamines The present application relates to novel insecticidal derivatives of substituted benzylamines, to processes for their preparation and to their use for controlling animal pests, especially arthropods, in particular insects. 5 Insecticidal and acaricidal benzylamino heterocyclic derivatives of the general formula R 5 2 R N R N -fD R1 wherein R is 1-naphthyl, phenyl or phenyl substituted with one or two substituents selected from halogen or (CI-C 2 ) alkyl; 10 R' is selected from hydrogen, (C 1

-C

4 ) alkyl and (CI-C 2 ) haloalkyl; R 2 is hydrogen; R 5 is se lected from cyano, (C 1

-C

2 ) alkoxy(CI-C 2 ) alkyl, 4-(C 1

-C

2 ) alkoxybenzyl, R R7 R10 0 X -P\ -C-O Ri1 1 N-R 1 R14, X H (1) (3) (5) X -S(O)a jR16 R15 H (6) (7) (9) where X is oxygen or sulfur; R 7 and R 8 are (C 1

-C

2 ) alkoxy or (CI-C 2 ) haloalkyl; R' 0 is hydrogen; R" 15 is (C 1

-C

4 ) alkyl; R1 3 is (CI-C 2 ) alkyl; R 1 4 is hydrogen or (C 1

-C

2 ) alkyl; a is 2; R 1 5 is (Ci-C 2 ) alkyl or (C 1

-C

2 ) dialkylamino; R1 6 is (Ci-C 2 ) alkyl or (Ci-C 2 ) alkoxy; and R1 9 is (C 1

-C

2 ) al kyl or (CI-C 2 ) alkoxy; provided that when R is 1-naphthyl and R 5 is formula (5) where X is sulfur, R1 3 is methyl and R' 4 WO 2008/119511 PCT/EP2008/002475 -2 is hydrogen, then R' is other than (C 1

-C

2 ) alkyl; and when R is 3-chloro-2-methylphenyl and R' is hydrogen, then R5 is other than formula (5) where X is oxygen, R1 3 is methyl and R' 4 is hydrogen or formula (6) where a is 2 and R' 5 is methyl, are described as one embodiment in WO 2006/127426 (cf. e.g. formula IB, page 8). 5 There is however a continuing demand for new insecticides and acaricides that are not only safer and less costly than the known compounds but are in particular more effective. This invention now provides novel compounds of the formula (I) R1 R6 R70 R9 R R R 7 O RS R 2 N N \8 R R 4 in which 10 R', R 2 , R', R 4 , and R 5 independently from each other represent hydrogen, halogen, hydroxy, alkyl, alkoxy, haloalkyl, alkoxyalkyl, cycloalkyl, cyanoalkyl, haloalkoxy, alkylthio, haloalkyl thio, alkylsulfonyl, alkylsulfonyloxy, halogenalkylsulfonyl, halogenalkylsulfonyloxy, alkoxycarbonyl, acetyl, alkylcarbonyl, alkenylcarbonyl, pentafluorosulfanyl, amino, mono and dialkylamino, cycloalkylamino, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cyano, or 15 nitro, or represent independently from each other aryl, aryloxy or heteroaryl which are op tionally substituted with one or more substituents selected from halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, nitro, and cyano; R6 and R7 independently from each other represent hydrogen, alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkylmercaptoalkyl, alkenyl, or alkynyl, or represent independently from each 20 other aryl, heteroaryl or heterocyclyl, optionally substituted with one or more substituents selected from halogen, alkyl, alkoxy, nitro, and cyano; R represents -C(Z)R' 0 , -C(Z)OR' 0 , or -C(Z)NR"R 1; Z represents 0 or S;

R

9 represents hydrogen, alkyl, or haloalkyl; WO 2008/119511 PCT/EP2008/002475 -3 R1 0 represents CI-C 2 ailcyl, substituted with one or more substituents selected from halogen, alkoxy, alkylmercapto and cyano, or represents C 3

-C

6 alkyl, cycloalkyl, or benzyl, option ally substituted with one or more substituents selected from halogen, and alkoxy; R" represents C 1

-C

2 alkyl, substituted with one or more substituents selected from halogen, 5 alkoxy, alkylmercapto, alkoxycarbonyl, alkylsulfmyl, alkylsulfonyl and cyano, or repre sents C 3

-C

8 alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, or alkynyl, optionally substituted with one or more substituents selected from halogen, haloalkyl, alkoxy, alkylmercapto, al kylsulfinyl, alkylsulfonyl, dialkylamino, alkoxycarbonyl, and dialkylaminocarbonyl, or represents arylalkyl, heterocyclyl, heterocyclylalkyl, aryl, heteroaryl, or heteroarylalkyl, 10 optionally substituted with one or more substituents selected from halogen, alkyl, halo genalkyl, alkoxy, halogenalkoxy, alkoxycarbonyl, heterocyclyl, dialkylaminoca'rbonyl, cyano, nitro, dialkylamino, S(O)n-alkyl, and S(O)n-halogenalkyl; R1 2 represents hydrogen or alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted with one or more substituents selected from halogen, alkoxy, alkylmercapto, cyano, alkylsulfinyl, 15 alkylsulfonyl, dialkylamino, alkoxycarbonyl, and dialkylaminocarbonyl, or represents ary lalkyl, heterocyclylalkyl, aryl, or heteroaryl, optionally substituted with one or more sub stituents selected from halogen, alkyl, halogenalkyl, alkoxy, halogenalkoxy, alkoxycar bonyl, dialkylaminocarbonyl, cyano, nitro, dialkylamino, S(O),-alkyl, and S(O)n halogenalkyl; and 20 n is 0, 1 or 2. Depending inter alia on the nature of the substituents, the compounds of the present invention may be present as geometrical and/or as optically active isomers or corresponding isomer mixtures of varying composition. Molecules that are not superimposable on their mirror image are called chiral; these molecules are optically active. If a molecule is nonsuperimposible on its mirror im 25 age, the mirror image must be a different molecule, since superimposability is the same as identity. In each case of optical activity of a pure compound there are two and only two isomers, called enantiomers, which differ in structure only in the left- and right-handedness of their orientations. Enantiomers differ in that they rotate the plane of polarized light in opposite directions and in that they react at different rates with other chiral compounds or in the presence of a chiral catalyst (cf. 30 March's Advanced Organic Chemistry 5th edition ; Wiley 2001 page 125-126). Provided that substituents R 6 and R 7 are different, the C-atom they are attached to is asymmetric or chiral and the respective compound is optically active. According to the Cahn-Ingold-Prelog sys tem that ranks the four groups on an asymmetric carbon atom in order of decreasing atomic num- WO 2008/119511 PCT/EP2008/002475 -4 ber, the asymmetric C-atom is present in S- or R-configuration (cf. March's Advanced Organic Chemistry 5th edition ; Wiley 2001 page 139). Compounds in which rotation is restricted may exhibit cis-trans isomerism. One type of cis-trans isomerism results from double bonds, such as the N=Oxazolidine-double bond. Based on the Cahn 5 Ingold-Prelog system, ranking the groups at each atom of the double bond in order of decreasing atomic number, the compounds according to the invention can be present in the Z or E form, Z being the isomer with the two higher ranking groups on the same side of the double bond (cf. March's Advanced Organic Chemistry 5th edition; Wiley 2001 page 157-158). R2 R 1R 6 R7 R 2 R 1R 6 R 7 R 8 R R Re"R R N R9 R3 N R3 N R4 R 5 R8 4 Rs O R RR (Z) (E) 10 Formula (I) of the present invention comprises both the pure R and S enantiomers and the enanti omer mixtures or racemates. Preferred are compounds of formula (Ib) R R R 7 O R9 2 R N N \ 8 R R R4 (Ib) in which R' to R9 are as defined above for formula (I). Depending on the actual substituents R' to R7, the asymmetric C-atom might be present in the R- or the S-configuration. 15 There is no disclosure or suggestion in WO 2006/127426 of the structures of the novel compounds of formula (I) of the present invention. In particular, there is no disclosure or suggestion in in WO 2006/127426 of the surprisingly and significantly improved insecticidal activity of the compounds of formula (Ib) over their optical antipodes or the racemates, respectively. As used herein, the "optical antipode" of an S-enantiomer is defined as the corresponding R 20 enantiomer that differs only in the configuration of the asymmetric C-atom and rotates the plane of polarized light in the opposite direction. Accordingly, the optical antipode of an R-enantiomer is WO 2008/119511 PCT/EP2008/002475 -5 the corresponding S-enantiomer. The formula (I) provides a general definition of the compounds according to the invention. Preferred substituents or ranges of the radicals given in the formulae mentioned above and below are illustrated below. 5 According to a further preferred embodiment of the invention, R1, R2, R3, R4, and R5 of formula (I) independently from each other represent hydrogen, halogen, preferably chlorine or fluorine, hydroxy, C 1

-C

4 alkyl, preferably C 1

-C

2 alkyl, CI-C 4 alkoxy, preferably C 1

-C

2 alkoxy, C 1

-C

4 haloalkyl, preferably C 1

-C

2 haloalkyl, (C 1

-C

4 )alkoxy(C 1 C 4 )alkyl, preferably (C 1

-C

2 )alkoxy(C 1

-C

2 )alkyl, C 3

-C

8 cycloalkyl, preferably C 3

-C

6 10 cycloalkyl, cyano(C 1

-C

4 )alkyl, preferably cyano(C 1

-C

2 )alkyl, halo(C 1

-C

4 )alkoxy, prefera bly halo(C 1

-C

2 )alkoxy, C 1

-C

4 alkylthio, preferably C 1

-C

2 alkylthio, halo(C 1

-C

4 )alkylthio, preferably halo(C 1

-C

2 )alkylthio, C 1

-C

4 alkylsulfonyl, preferably C 1

-C

2 alkylsulfonyl, CI-C 4 alkylsulfonyloxy, preferably C 1

-C

2 alkylsulfonyloxy, halogen(C 1

-C

4 )alkylsulfonyl, pref erably halogen(C 1

-C

2 )alkylsulfonyl, halogen(C 1

-C

4 )alkylsulfonyloxy, preferably halo 15 gen(C 1

-C

2 )alkylsulfonyloxy, C 1

-C

4 alkoxycarbonyl, preferably C 1

-C

2 alkoxycarbonyl, ace tyl, C 1

-C

4 alkylcarbonyl, preferably C 1

-C

2 alkylcarbonyl, C 2

-C

4 alkenylcarbonyl, penta fluorosulfanyl, amino, mono- and di(C 1 -C4)alkylamino, preferably mono- and di(C 1 C 2 )alkylamino, C 3

-C

8 cycloalkylamino, preferably C 3

-C

6 cycloalkylamino, C 2

-C

4 alkenyl, halo(C 2

-C

4 )alkenyl, C 2

-C

4 alkynyl, halo(C 2

-C

4 )alkynyl, cyano, or nitro, or represent inde 20 pendently from each other C 5 -Cs aryl, preferably C 5

-C

6 aryl, C 5

-C

8 aryloxy, preferably C 5 C 6 aryloxy, or heteroaryl comprising a 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P, and S, which are optionally substituted with one or more substituents selected from halogen, C 1

-C

4 alkyl, preferably C 1

-C

2 alkyl, halo(C 1 C 4 )alkyl, preferably halo(C 1

-C

2 )alkyl, C 1

-C

4 alkoxy, preferably CI-C 2 alkoxy, halo(C 1 25 C 4 )alkoxy, preferably halo(C 1

-C

2 )alkoxy, C 1

-C

4 alkoxycarbonyl, preferably C 1

-C

2 alkoxy carbonyl, nitro, and cyano;

R

6 and R7 independently from each other represent hydrogen, C 1

-C

4 alkyl, preferably C 1

-C

2 alkyl,

C

1

-C

4 haloalkyl, preferably C 1

-C

2 haloalkyl, C 3

-C

8 cycloalkyl, preferably C 3

-C

6 cycloalkyl,

(C

1

-C

4 )alkoxy(C 1

-C

4 )alkyl, preferably (C 1

-C

2 )alkoxy(C 1

-C

2 )alkyl, C 1

-C

4 alkylmercapto(C 1 30 C 4 )alkyl, preferably C 1

-C

2 alkylmercapto(C 1

-C

2 )alkyl, C 2

-C

4 alkenyl, or C 2

-C

4 alkynyl, or represent independently from each other C 5

-C

8 aryl, preferably C 5

-C

6 aryl, heteroaryl com prising a 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P, and S, or heterocyclyl comprising a 5-8 membered ring containing one, two or more WO 2008/119511 PCT/EP2008/002475 -6 heteroatoms selected from 0, N, P, and S, optionally substituted with one or more sub stituents selected from halogen, C 1

-C

4 alkyl, preferably C 1

-C

2 alkyl, C 1

-C

4 alkoxy, prefera bly C 1

-C

2 alkoxy, nitro, and cyano;

R

8 represents -C(Z)R 0 , -C( Z)OR'", or -C(Z)NR"R' 2 ; 5 Z represents 0 or S;

R

9 represents hydrogen, C 1

-C

4 alkyl, preferably C 1

-C

2 alkyl, or C 1

-C

4 haloalkyl, preferably C 1 C 2 haloalkyl; R1 0 represents C 1

-C

2 alkyl, substituted with one or more substituents selected from halogen,

C

1

-C

4 alkoxy, preferably C 1

-C

2 alkoxy, C 1

-C

4 alkylmercapto, preferably C 1

-C

2 alkylmer 10 capto, and cyano, or represents C 3

-C

6 alkyl, C 3

-C

6 cycloalkyl, or benzyl, optionally substi tuted with one or more substituents selected from halogen, and C 1

-C

4 alkoxy, preferably

C

1

-C

2 alkoxy; R" represents C 1

-C

2 alkyl, substituted with one or more substituents selected from halogen,

C

1

-C

4 alkoxy, preferably C 1

-C

2 alkoxy, C 1

-C

4 alkylmercapto, preferably C 1

-C

2 alkylmer 15 capto, C 1

-C

4 alkoxycarbonyl, preferably C 1

-C

2 alkoxycarbonyl, C 1

-C

4 alkylsulfinyl, pref erably C 1

-C

2 alkylsulfinyl, C 1

-C

4 alkylsulfonyl, preferably C 1

-C

2 alkylsulfonyl, and cyano, or represents C 3

-C

8 alkyl, C 3

-C

6 cycloalkyl, (C 3

-C

6 )cycloalkyl(C 1

-C

4 )alkyl, C 2

-C

4 alkenyl, or C 2

-C

4 alkynyl, optionally substituted with one or more substituents selected from halo gen, halo(C 1 -C4)alkyl, preferably halo(C 1

-C

2 )alkyl, C 1

-C

4 alkoxy, preferably C 1

-C

2 alkoxy, 20 C1-C 4 alkylmercapto, preferably C 1

-C

2 alkylmercapto, C 1

-C

4 alkylsulfmyl, preferably C 1

-C

2 alkylsulfinyl, C 1

-C

4 alkylsulfonyl, preferably C 1

-C

2 alkylsulfonyl, di(C 1

-C

4 )alkylamino, preferably di(C 1

-C

2 )alkylamino, C 1

-C

4 alkoxycarbonyl, preferably C 1

-C

2 alkoxycarbonyl, and di(C 1

-C

4 )alkylaminocarbonyl, preferably di(C 1

-C

2 )alkylaminocarbonyl, or represents

C

5

-C

8 aryl(C 1 -C4)alkyl, preferably C 5

-C

6 aryl(C 1

-C

2 )alcyl, heterocyclyl comprising a 5-8 25 membered ring containing one, two or more heteroatoms selected from 0, N, P and S, het erocyclyl(C 1 -C4)alkyl, preferably heterocyclyl(C-C 2 )alkyl, the heterocyclyl comprising a 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P, and S,

C

5 -Cs aryl, heteroaryl comprising a 5-8 membered ring containing one, two or more het eroatoms selected from 0, N, P, and S, or heteroaryl(C 1

-C

4 )alkyl, preferably heteroaryl(C 1 30 C 2 )alkyl, the heteroaryl comprising a 5-8 membered ring containing one, two or more het eroatoms selected from 0, N, P, and S, optionally substituted with one or more substituents selected from halogen, Ci-C 4 alkyl, preferably C 1

-C

2 alkyl, halogen(C 1

-C

4 )alkyl, preferably halogen(C 1

-C

2 )alkyl, C 1

-C

4 alkoxy, preferably C 1

-C

2 alkoxy, halogen(C 1

-C

4 )alkoxy, pref- WO 2008/119511 PCT/EP2008/002475 -7 erably halogen(CI-C 2 )alkoxy, CI-C 4 alkoxycarbonyl, preferably C 1

-C

2 alkoxycarbonyl, het erocyclyl comprising a 5-8 membered ring containing one, two or more heteroatoms se lected from 0, N, P, and S, di(Ci-C 4 )alkylaminocarbonyl, preferably di(C 1 C 2 )alkylaminocarbonyl, cyano, nitro, di(CI-C 4 )alkylamino, preferably di-(C 1 5 C 2 )alkylamino, S(O)n-(CI-C 4 )alkyl, preferably S(O)n-(C 1

-C

2 )alkyl, and S(O)n-halogen(Ci

C

4 )alkyl, preferably S(O)n-halogen(CI-C 2 )alkyl;

R

12 represents hydrogen or C 1

-C

4 alkyl, preferably Ci-C 2 alkyl, C 3

-C

8 cycloalkyl, preferably

C

3

-C

6 cycloalkyl, C 2

-C

4 alkenyl, C 2

-C

4 alkynyl, optionally substituted with one or more substituents selected from halogen, CI-C 4 alkoxy, preferably C 1

-C

2 alkoxy, C 1

-C

4 alkyl 10 mercapto, preferably C 1

-C

2 alkylmercapto, cyano, CI-C 4 alkylsulfmyl, preferably C 1

-C

2 al kylsulfinyl, C 1

-C

4 alkylsulfonyl, preferably C 1

-C

2 alkylsulfonyl, di(CI-C 4 )alkylamino, pref erably di(C 1

-C

2 )alkylamino, C 1

-C

4 alkoxycarbonyl, preferably C 1

-C

2 alkoxycarbonyl, and di(CI-C 4 )alkylaminocarbonyl, preferably di(CI-C 2 )alkylaminocarbonyl, or represents C 5 -Cg aryl(Ci-C 4 )alkyl, heterocyclyl(Ci-C 4 )alkyl, preferably heterocyclyl(C 1

-C

2 )alkyl, the hetero 15 cyclyl comprising a 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P, and S, C 5

-C

8 aryl, or heteroaryl comprising a 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P, and S, optionally substituted with one or more substituents selected from halogen, C 1

-C

4 alkyl, preferably CI-C 2 alkyl, halo gen(Ci-C 4 )alkyl, preferably halogen(C 1

-C

2 )alkyl, CI-C 4 alkoxy, preferably C 1

-C

2 alkoxy, 20 halogen(C 1

-C

4 )alkoxy, preferably halogen(CI-C 2 )alkoxy, CI-C 4 alkoxycarbonyl, preferably C1-C2 alkoxycarbonyl, di(C 1

-C

4 )alkylaminocarbonyl, preferably di(Ci

C

2 )alkylaminocarbonyl, cyano, nitro, di(C 1

-C

4 )alkylamino, preferably di-(C

C

2 )alkylamino, S(O),-(CI-C 4 )alkyl, preferably S(O),-(C 1

-C

2 )alkyl, and S(O),-halogen(C 1 C4)alkyl, preferably S(O)n-halogen(Ci-C 2 )alkyl; and 25 n is 0, 1 or 2 Further preferred are compounds of formula (Ib) in which R' to R9 are as defined above for the preferred embodiment of formula (I) and the special group therof. As used herein, "alkyl" is defined as a straight or branched C 112 alkyl such as, for example, methyl, ethyl, n- or iso 30 propyl, n-, iso-, sec- or tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl and the like, preferably, a C 1

.

6 alkyl, more preferably, a CI.4 alkyl. "alkenyl" is defined as a straight or branched C 2

-

12 alkenyl comprising at least one double bond WO 2008/119511 PCT/EP2008/002475 -8 such as, for example, vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3 butanedienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3 pentanedienyl, 1-hexenyl, 2 hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1,4-hexanedienyl, and the like, preferably, a C 2

-

6 al kenyl, more preferably a C 2 -4 alkenyl. 5 "alkynyl" is defined as a C 2

-

1 2 alkynyl comprising at least one triple bond and optionally further comprising one or more double bonds such as, for example, ethynyl, 1 -propynyl, propargyl and the like, preferably, a C 2

-

6 alkynyl, more preferably a C24 alkynyl. As each alkyl portion in "alkoxy", "haloalkyl", "alkoxyalkyl", "alkylaminocarbonyl", "dialkylami noalkyl", "haloalkoxy", "alkoxycarbonyl", "alkoxycarbonyl" and "alkoxycarbonylalkyl", and the 10 like, the same portions as described in the above-mentioned alkyll" are exemplified. "cycloalkyl" is defined as a C 3

_

8 cycloalkyl such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like, preferably, a C 3

-

6 cycloalkyl. "heterocycloalkyl" (= "heterocyclyl") is defined as a cycloalkyl comprising a 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P, and S, such as tetrahydrofurane, 15 thiolane, pyrrolidine, oxathiolane, oxazolidine, tetrahydropurane, piperidine, oxetane, tetrahy drothiophendioxide, dioxane, and the like, preferred is tetrahydrofurane. "aryl" is defined as an unsaturated C 5

-CI

2 cycloalkyl, such as phenyl, a- or p-naphthyl, preferably, phenyl. "heteroaryl" is defined as an aryl comprising a 5-8 membered ring containing one, two or more 20 heteroatoms selected from 0, N, P, and S, such as furane, thiophene, pyrrole, oxazole, thiazole, pyrazole, pyridine, pyrimidine, pyrazole and the like, preferred are pyrimidine and pyrrazole. "aralkyl" is defined as, for example, benzyl, phenethyl or a-methylbenzyl, preferably, benzyl. "halogen" is defined as fluorine, chlorine, bromine or iodine, preferably, fluorine, or chlorine. As each halogen portion in "haloalkyl", "haloalkoxy", "haloalkylthio", "halogenalkylsulfonyl", 25 "halogenalkylsulfonyloxy", "haloalkenyl", "haloalkynyl", and the like, the same portions as de scribed above are exemplified. According to a particularly preferred embodiment, R', R2, R , R4, and R' of the formula (I) independently from each other represent hydrogen, halo gen, alkyl, alkoxy, haloalkyl, alkoxyalkyl, cycloalkyl, haloalkoxy, alkylthio, haloalkylthio, alkyl- WO 2008/119511 PCT/EP2008/002475 -9 sulfonyl, alkylsulfonyloxy, halogenalkylsulfonyl, alkoxycarbonyl, acetyl, alkylcarbonyl, alkenyl carbonyl, dialkylamino, cycloalkylamino, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cyano, or nitro; R6 and R7 independently from each other represent hydrogen, alkyl, haloalkyl, cycloalkyl, 5 alkoxyalkyl, alkylmercaptoalkyl, alkenyl, or alkynyl, or independently from each other represent aryl, optionally substituted with one or more substituents selected from halogen, alkyl, alkoxy, nitro and cyano; R8 represents -C(Z)NR"R 12 ; Z represents 0 or S; 10 R9 represents hydrogen, or alkyl; R"1 represents C 1

-C

2 alkyl, substituted with one or more substituents selected from halogen, alkoxy, alkylmercapto, alkoxycarbonyl, alkylsulfinyl, alkylsulfonyl and cyano, or repre sents C 3

-C

8 alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, or alkynyl, optionally substituted with one or more substituents selected from halogen, haloalkyl, alkoxy, alkylmercapto, al 15 kylsulfinyl, alkylsulfonyl, dialkylamino, alkoxycarbonyl, and dialkylaminocarbonyl, or represents arylalkyl, heterocyclyl, heterocyclylalkyl, aryl, heteroaryl, or heteroarylalkyl, optionally substituted with one or more substituents selected from halogen, alkyl, halo genalkyl, alkoxy, halogenalkoxy, alkoxycarbonyl, heterocyclyl, dialkylaminocarbonyl, cyano, nitro, dialkylamino, S(O),-alkyl, and S(O).-halogenalkyl; 20 R represents hydrogen or alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted with one or more substituents selected from halogen, alkoxy, alkylmercapto, cyano, alkylsulfinyl, alkylsulfonyl, dialkylamino, alkoxycarbonyl, and dialkylaminocarbonyl, or represents ary lalkyl, heterocyclylalkyl, aryl, or heteroaryl, optionally substituted with one or more sub stituents selected from halogen, alkyl, halogenalkyl, alkoxy, halogenalkoxy, alkoxycar 25 bonyl, dialkylaminocarbonyl, cyano, nitro, dialkylamino, S(O).-alkyl, and S(O)n halogenalkyl; n is0,1 or2 According to a special group of compounds of the particularly preferred embodiment defined above, WO 2008/119511 PCT/EP2008/002475 - 10 R', R2, R 3 , R4, and R' of formula (I) independently from each other represent hydrogen, halogen, preferably chlorine or fluorine, CI-C 4 alkyl, preferably C 1

-C

2 alkyl, C 1

-C

4 alkoxy, prefera bly C 1

-C

2 alkoxy, C 1

-C

4 haloalkyl, preferably CI-C 2 haloalkyl, (C 1

-C

4 )alkoxy(C 1

-C

4 )alkyl, preferably (Ci-C 2 )alkoxy(C 1

-C

2 )alkyl, C 3

-C

8 cycloalkyl, preferably C 3

-C

6 cycloalkyl, 5 halo(C 1

-C

4 )alkoxy, preferably halo(CI-C 2 )alkoxy, C 1

-C

4 alkylthio, preferably C 1

-C

2 alkyl thio, halo(C 1

-C

4 )alkylthio, preferably halo(C 1

-C

2 )alkylthio, C 1

-C

4 alkylsulfonyl, preferably

C

1

-C

2 alkylsulfonyl, C 1

-C

4 alkylsulfonyloxy, preferably CI-C 2 alkylsulfonyloxy, halo gen(C 1

-C

4 )alkylsulfonyl, preferably halogen(C 1

-C

2 )alkylsulfonyl, C 1

-C

4 alkoxycarbonyl, preferably CI-C 2 alkoxycarbonyl, acetyl, CI-C 4 alkylcarbonyl, preferably C 1

-C

2 alkylcar 10 bonyl, C 2

-C

4 alkenylcarbonyl, di(C 1 -C4)alkylamino, preferably di(CI-C 2 )alkylamino, C 3

-C

8 cycloalkylamino, preferably C 3

-C

6 cycloalkylamino, C 2

-C

4 alkenyl, halo(C 2

-C

4 )alkenyl, C 2 C 4 alkynyl, halo(C 2

-C

4 )alkynyl, cyano, or nitro; R6 and R7 independently from each other represent hydrogen, C 1

-C

4 alkyl, preferably CI-C 2 alkyl,

C

1

-C

4 haloalkyl, preferably C 1

-C

2 haloalkyl, C 3

-C

8 cycloalkyl, preferably C 3

-C

6 cycloalkyl, 15 (C 1

-C

4 )alkoxy(C 1

-C

4 )alkyl, preferably (CI-C 2 )alkoxy(CI-C 2 )alkyl, C 1

-C

4 alkylmercapto(C 1 C 4 )alkyl, preferably C 1

-C

2 alkylmercapto(C 1

-C

2 )alkyl, C 2

-C

4 alkenyl, or C 2

-C

4 alkynyl, or represent independently from each other C 5

-C

8 aryl, preferably C 5

-C

6 aryl, optionally sub stituted with one or more substituents selected from halogen, preferably chlorine or fluo rine, CI-C 4 alkyl, preferably C 1

-C

2 alkyl, C 1

-C

4 alkoxy, preferably C 1

-C

2 alkoxy, nitro and 20 cyano; R8 represents -C(Z)NR"R12; Z represents 0 or S;

R

9 represents hydrogen, or CI-C 4 alkyl, preferably C 1

-C

2 alkyl; R" represents C 1

-C

2 alkyl, substituted with one or more substituents selected from halogen, 25 Cl-C 4 alkoxy, preferably C 1

-C

2 alkoxy, C 1

-C

4 alkylmercapto, preferably C 1

-C

2 alkylmer capto, CI-C 4 alkoxycarbonyl, preferably C 1

-C

2 alkoxycarbonyl, CI-C 4 alkylsulfinyl, pref erably C 1

-C

2 alkylsulfmyl, C 1

-C

4 alkylsulfonyl, preferably C 1

-C

2 alkylsulfonyl, and cyano, or represents C 3

-C

8 alkyl, C 3

-C

6 cycloalkyl, (C 3

-C

6 )cycloalkyl(C 1

-C

4 )alkyl, C 2

-C

4 alkenyl, or C 2

-C

4 alkynyl, optionally substituted with one or more substituents selected from halo 30 gen, halo(C 1

-C

4 )alkyl, preferably halo(C 1

-C

2 )alkyl, C 1

-C

4 alkoxy, preferably C 1

-C

2 alkoxy,

CI-C

4 alkylmercapto, preferably C 1

-C

2 alkylmercapto, CI-C 4 alkylsulfinyl, preferably Ci-C 2 alkylsulfinyl, CI-C 4 alkylsulfonyl, preferably CI-C 2 alkylsulfonyl, di(CI-C 4 )alkylamino, preferably di(C 1

-C

2 )alkylamino, C 1

-C

4 alkoxycarbonyl, preferably CI-C 2 alkoxycarbonyl, WO 2008/119511 PCT/EP2008/002475 - 11 and di(C 1

-C

4 )alkylaminocarbonyl, preferably di(C 1

-C

2 )alkylaminocarbonyl, or represents

C

5

-C

8 aryl(C 1

-C

4 )alkyl, preferably C 5

-C

6 aryl(CI-C 2 )alkyl, heterocyclyl comprising a 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P and S, het erocyclyl(C 1

-C

4 )alkyl, preferably heterocyclyl(C 1

-C

2 )alkyl, the heterocyclyl comprising a 5 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P, and S,

C

5 -Cs aryl, heteroaryl comprising a 5-8 membered ring containing one, two or more het eroatoms selected from 0, N, P, and S, or heteroaryl(C 1

-C

4 )alkyl, preferably heteroaryl(C 1 C 2 )alkyl, the heteroaryl comprising a 5-8 membered ring containing one, two or more het eroatoms selected from 0, N, P, and S, optionally substituted with one or more substituents 10 selected from halogen, CI-C 4 alkyl, preferably C 1

-C

2 alkyl, halogen(CI-C 4 ) alkyl, prefera bly halogen(C 1

-C

2 )alkyl, CI-C 4 alkoxy, preferably C 1

-C

2 alkoxy, halogen(C 1

-C

4 )alkoxy, preferably halogen(C 1

-C

2 )alkoxy, CI-C 4 alkoxycarbonyl, preferably CI-C 2 alkoxycarbonyl, heterocyclyl comprising a 5-8 membered ring containing one, two or more heteroatoms se lected from 0, N, P, and S, di(C 1

-C

4 )alkylaminocarbonyl, preferably di(C 1 15 C 2 )alkylaminocarbonyl, cyano, nitro, di(C 1

-C

4 )alkylamino, preferably di-(C 1 C 2 )alkylamino, S(O)n-(C 1

-C

4 )alkyl, preferably S(O)n-(Ci-C 2 )alkyl, and S(O),-halogen(C 1 C 4 )alkyl, preferably S(O)n-halogen(C 1

-C

2 )alkyl; R2 represents hydrogen or C1-C4 alkyl, preferably C 1

-C

2 alkyl, C 3 -Cs cycloalkyl, preferably

C

3

-C

6 cycloalkyl, C 2

-C

4 alkenyl, C 2

-C

4 alkynyl, optionally substituted with one or more 20 substituents selected from halogen, C 1

-C

4 alkoxy, preferably C 1

-C

2 alkoxy, CI-C 4 alkyl mercapto, preferably C 1

-C

2 alkylmercapto, cyano, C 1

-C

4 alkylsulfinyl, preferably C 1

-C

2 al kylsulfmyl, CI-C 4 alkylsulfonyl, preferably C 1

-C

2 alkylsulfonyl, di(C 1

-C

4 )alkylamino, pref erably di(Ci-C 2 )alkylamino, C 1

-C

4 alkoxycarbonyl, preferably C 1

-C

2 alkoxycarbonyl, and di(C 1 -C4)alkylaminocarbonyl, preferably di(C 1

-C

2 )alkylaminocarbonyl, or represents C 5 -Cs 25 aryl(C 1

-C

4 )alkyl, heterocyclyl(C 1

-C

4 )alkyl, preferably heterocyclyl(C 1

-C

2 )alkyl, the hetero cyclyl comprising a 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P, and S, C 5

-C

8 aryl, heteroaryl comprising a 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P, and S, optionally substituted with one or more substituents selected from halogen, C 1

-C

4 alkyl, preferably C 1

-C

2 alkyl, halo 30 gen(C 1

-C

4 )alkyl, preferably halogen(CI-C 2 )alkyl, CI-C 4 alkoxy, preferably C 1

-C

2 alkoxy, halogen(C 1

-C

4 )alkoxy, preferably halogen(C 1

-C

2 )alkoxy, CI-C 4 alkoxycarbonyl, preferably CI-C2 alkoxycarbonyl, di(C 1

-C

4 )alkylaminocarbonyl, preferably di(C 1 C 2 )alkylaminocarbonyl, cyano, nitro, di(Ci-C 4 )alkylamino, preferably di-(C 1 C 2 )alkylamino, S(O)n-( Cl-C 4 )alkyl, preferably S(O).-(C 1

-C

2 )alkyl, and S(O)n-halogen(C 1 35 C 4 )alkyl, preferably S(O).-halogen(CI-C 2 )alkyl; and WO 2008/119511 PCT/EP2008/002475 - 12 n is 0, 1 or 2 Further preferred are compounds of formula (Ib) in which R' to R9 are as defined above for the particularly preferred embodiment of formula (I) and the special group therof. According to a very particularly preferred embodiment of the invention, 5 R', R 2 , R 3 , R 4 , and R' of formula (I) independently from each other represent hydrogen, halogen, alkyl, alkoxy, haloalkyl; or haloalkoxy;

R

6 and R 7 independently from each other represent hydrogen, alkyl, or haloalkyl; R represents -C(S)NR"R1 2 ; R9 represents hydrogen; 10 R" represents C 1

-C

2 alkyl, substituted with one or more substituents selected from halogen, alkoxy, alkylmercapto, alkoxycarbonyl, alkylsulfinyl, alkylsulfonyl, or cyano, or represents

C

3 -Cs alkyl, cycloalkyl, cycloalkylalkyl, or alkenyl, optionally substituted with one or more substituents selected from halogen, haloalkyl, alkoxy, alkylmercapto, alkylsulfinyl, alkyl sulfonyl, and alkoxycarbonyl, or represents arylalkyl, heterocyclyl, heterocyclylalkyl, aryl, 15 heteroaryl, or heteroarylalkyl, optionally substituted with one or more substituents selected from halogen, alkyl, halogenalkyl, alkoxy, halogenalkoxy, alkoxycarbonyl, and heterocy clyl; R2 represents hydrogen; According to a special group of compounds of the very particularly preferred embodiment defined 20 above, R', R2, R3, R, and R' of formula (I) independently from each other represent hydrogen, halogen, preferably chlorine or fluorine, C 1

-C

4 alkyl, preferably C 1

-C

2 alkyl, C 1

-C

4 alkoxy, prefera bly C 1

-C

2 alkoxy, C 1

-C

4 haloalkyl, preferably C 1

-C

2 haloalkyl; C 1

-C

4 haloalkoxy, prefera bly C 1

-C

2 haloalkoxy; 25 R 6 and R 7 independently from each other represent hydrogen, C 1

-C

4 alkyl, preferably C 1

-C

2 alkyl,

C

1

-C

4 haloalkyl, preferably C 1

-C

2 haloalkyl;

R

8 represents -C(S)NR"R1 2 ; R9 represents hydrogen; WO 2008/119511 PCT/EP2008/002475 - 13 R" represents C 1

-C

2 alkyl, substituted with one or more substituents selected from halogen,

C

1

-C

4 alkoxy, preferably C 1

-C

2 alkoxy, CI-C 4 alkylmercapto, preferably C 1

-C

2 alkylmer capto, C 1

-C

4 alkoxycarbonyl, preferably C 1

-C

2 alkoxycarbonyl, C 1

-C

4 alkylsulfmyl, pref erably C 1

-C

2 alkylsulfmyl, C 1

-C

4 alkylsulfonyl, preferably C 1

-C

2 alkylsulfonyl, and cyano, 5 or represents C 3 -Cs alkyl, C 3

-C

6 cycloalkyl, (C 3

-C

6 )cycloalkyl(C 1

-C

4 )alkyl, C 2

-C

4 alkenyl, optionally substituted with one or more substituents selected from halogen, halo(C 1 C 4 )alkyl, preferably halo(C 1

-C

2 )alkyl, C 1

-C

4 alkoxy, preferably C 1

-C

2 alkoxy, C 1

-C

4 alkyl mercapto, preferably C 1

-C

2 alkylmercapto, CI-C 4 alkylsulfmyl, preferably C 1

-C

2 alkyl sulfinyl, CI-C 4 alkylsulfonyl, preferably C 1

-C

2 ailcylsulfonyl, C 1

-C

4 alkoxycarbonyl, pref 10 erably C 1

-C

2 alkoxycarbonyl, or represents, heterocyclyl comprising a 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P, and S, heterocyclyl(C 1 C 4 )alkyl, preferably heterocyclyl(C 1

-C

2 )alkyl, the heterocyclyl comprising a 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P, and S, or C 5

-C

8 aryl; heteroary comprising a 5-8 membered ring containing one, two or more heteroatoms se 15 lected from 0, N, P and S, or heteroaryl (C 1

-C

4 ) alkyl, preferably heteroaryl (C 1

-C

2 ) alkyl, the heteroaryl comprising a 5-8 membered ring containing on, two or more heteroatoms se lected from 0, N, P and S, and R1 2 represents hydrogen. Further preferred are compounds of formula (Ib) in which R1 to R9 are as defied above for the 20 very particularly preferred embodiment of formula (I) and the special group therof. According to the most preferred embodiment of the invention, R', R2, R3, R4, and R5 of formula (I) independently from each other represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, or haloalkoxy; R6 represents alkyl; 25 R7 represents hydrogen;

R

8 represents -C(S)NR"R1; R' represents hydrogen; R" represents C 1

-C

2 alkyl, substituted with one or more substituents selected from halogen, alkoxy, alkylmercapto, alkoxycarbonyl, alkylsulfinyl, alkylsulfonyl, or cyano, or represents 30 C 3

-C

8 alkyl, cycloalkyl, cycloalkylalkyl, or alkenyl, optionally substituted with one or more WO 2008/119511 PCT/EP2008/002475 - 14 substituents selected from halogen, haloalkyl, alkoxy, alkylmercapto, alcylsulfinyl, alkyl sulfonyl, and alkoxycarbonyl, or represents arylalkyl, heterocyclyl, heterocyclylalkyl, aryl, heteroaryl, or heteroarylalkyl, optionally substituted with one or more substituents selected from halogen, alkyl, halogenalkyl, alkoxy, halogenalkoxy, alkoxycarbonyl,and heterocy 5 clyl; and

R

12 represents hydrogen. According to a special group of compounds of the most preferred embodiment defined above, R', R2, RW, R 4 , and R5 of formula (1) independently from each other represent hydrogen, halogen, preferably chlorine or fluorine, C 1

-C

4 alkyl, preferably C 1

-C

2 alkyl, C 1

-C

4 alkoxy, prefera 10 bly C 1

-C

2 alkoxy, CI-C 4 haloalkyl, preferably C 1

-C

2 haloalkyl, CI-C 4 haloalkoxy, prefera bly C 1

-C

2 haloalkoxy;

R

6 represents C 1

-C

4 alkyl, preferably C 1

-C

2 alkyl, R7 represents hydrogen;

R

8 represents -C(S)NR"R1 2 ; 15 R' represents hydrogen; R" represents C 1

-C

2 alkyl, substituted with one or more substituents selected from halogen,

CI-C

4 alkoxy, preferably C 1

-C

2 alkoxy, C 1

-C

4 alkylmercapto, preferably C 1

-C

2 alkylmer capto, C 1

-C

4 alkoxycarbonyl, preferably C 1

-C

2 alkoxycarbonyl, C 1

-C

4 alkylsulfinyl, pref erably C 1

-C

2 alkylsulfinyl, C 1

-C

4 alkylsulfonyl, preferably C 1

-C

2 alkylsulfonyl, and cyano, 20 or represents C 3

-C

8 alkyl, C 3

-C

6 cycloalkyl, (C 3

-C

6 )cycloalkyl(CI-C 4 )alkyl, C 2

-C

4 alkenyl, optionally substituted with one or more substituents selected from halogen, halo(Ci

C

4 )alkyl, preferably halo(C 1

-C

2 )alkyl, C 1

-C

4 alkoxy, preferably C 1

-C

2 alkoxy, C 1

-C

4 alkyl mercapto, preferably C 1

-C

2 alkylmercapto, CI-C 4 alkylsulfinyl, preferably Ci-C 2 alkyl sulfinyl, C 1

-C

4 alkylsulfonyl, preferably C 1

-C

2 alkylsulfonyl, C 1

-C

4 alkoxycarbonyl, pref 25 erably C 1

-C

2 alkoxycarbonyl, or represents heterocyclyl comprising a 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P, and S, heterocyclyl(C 1 C 4 )alkyl, preferably heterocyclyl(C 1

-C

2 )alkyl, the heterocyclyl comprising a 5-8 membered ring containing one, two or more heteroatoms selected from 0, N, P, and S, or C 5

-C

8 aryl; heteroaryl comprising a 5-8 membered ring containing one, two or more heteroatoms se 30 lected from 0, N, P and S, or heteroaryl (C 1

-C

4 ) alkyl, preferably heteroaryl (CI-C 2 ) alkyl, the heteroaryl comprising a 5-8 membered ring containing one, two or more heteroatoms WO 2008/119511 PCT/EP2008/002475 - 15 selected from 0, N, P and S, and R1 2 represents hydrogen. Further preferred are compounds of formula (Ib) in which R' to R9 are as defined above for the most preferred embodiment of formula (I) and the special group therof. All compounds of formula 5 (Ib) in which R 1 to R9 are as defined above for the most preferred embodiment of formula (I) and the special group therof are present in the S-configuration. The general or preferred radical definitions or explanations given above apply both to the end products and, correspondingly, to precursors and intermediates. These radical definitions can be combined with one another as desired, i.e. including combinations between the respective pre 10 ferred ranges. Preference according to the invention is given to compounds of the formula (I) or (Ib) which con tain a combination of the meanings listed above as being preferred. Particular preference according to the invention is given to compounds of the formula (I) or (Ib) which contain a combination of the meanings listed above as being particularly preferred. 15 Very particular preference according to the invention is given to compounds of the formula (I) or (Ib) which contain a combination of the meanings listed above as being very particularly preferred. Most preference according to the invention is given to compounds of the formula (I) or (Ib) which contain a combination of the meanings listed above as being most preferred. The present invention further relates to a composition comprising at least one compound of the 20 formula (I) or (Ib) as defined in any embodiment above and customary extenders and/or surfac tants. Customary extenders and surfactants are defined below. The present invention also relates to a method for controlling pests, wherein a compound of the formula (I) or (Ib) as defined in any embodiment above or a composition comprising at least one compound of the formula (I) or (Ib) as defined in any embodiment above and customary extenders 25 and/or surfactants is allowed to act on the pests and/or their habitat. Further, the present invention relates to the use of the compounds of the formula (I) or (Ib) as de fined in any embodiment above or of compositions comprising at least one compound of the for mula (I) or (Ib) as defined in any embodiment above and customary extenders and/or surfactants for controlling pests.

WO 2008/119511 PCT/EP2008/002475 - 16 The novel substituted compounds of the formula (1) or (Ib) in which R' is -C(S)NR"R 2 , and R 2 is hydrogen are obtained when a compound of the formula (II) or (fIb) R R R 7 R9 R1 R R O R9 2 R2 N N R 'N N 3* / H 3 / sH RR R (II) R(11b) 5 in which R', R2, R , R, R', R6, R 7 and R 9 are as defined above is reacted with a compound of formula (III) R"-NCS (III) in which 10 R" is as defined above, and N,N-di-isopropylethylamine in an aprotic solvent such as dichloromethane, chloroform, ace tonitrile, dimetylformamide, tetrahydrofuran, or ethyl acetate at temperatures from -20 to 120*C, preferably 20-60*C, depending on the solvent. Reaction times are 0.5 to 20 h, ratios of the educts are compound of formula II : compound of formula III of 1 : 1 to 1 : 1.5, preferably 1 : 1 (process 15 1). Furthermore, it has been found that the novel substituted compounds of the formula (I) or (Ib) in which R' is -C(S)NR"R 1 2 , and R1 2 is hydrogen can also be obtained when WO 2008/119511 PCT/EP2008/002475 - 17 a compound of the formula (II) or (IIb)

R

1 R R 7 R9 R1 R R 7 R9 2 N N R 'N N 3 H 3 / 5 H R R R R R4 (ii)

R

4 (11b) in which R', R2, R 3 , R 4 , R', R6, R7 and R9 are as defined above 5 is reacted with thiocarbonyldiimidazole N N N YN/ S and a compound of the formula (IV)

R"-NH

2 (IV) in which 10 R" is as defined above, in an aprotic solvent such as dichloromethane, chloroform, acetonitrile, dimetylformamide, tetra hydrofuran, or ethyl acetate at temperatures from -20 to 120 0 C, preferably 0-40*C, depending on the solvent. Reaction times are 1 to 20 h, ratios of the educts are compound of formula II : thiocar bonyldiimidazole : compound of formula III of 1 : 1: I to 1:2:2, preferably 1 : 1.1 : 1.1 (process 2). 15 This method is preferred if an isothiocyanate of an amine is not commercially available (e.g. ami noacetonitrile) and allows the use of the corresponding amine itself to shorten the synthesis path way. In general, the synthesis of thioureas by reaction of amines with thiocarbonyldiimidazole is known in the art (cf. e.g. WO 2005/007601, pages 50-52). However, the synthesis of 2-(imino)-1,3 20 oxazolidine-3-carbothioamides by reaction of an oxazolidine with thiocarbonyldiimidazole and a primary or secondary amine has not been described before. Surprisingly, it was found that this WO 2008/119511 PCT/EP2008/002475 - 18 reaction of an oxazolidine with thiocarbonyldiimidazole and a primary or secondary amine is fea sible. In view of the low basicity of the oxazolidines, this was unexpected for a person skilled in the art. The amines (IV), thiocarbonyldiimidazole and isothiocyanates (III) are generally known and com 5 mercially available. The compounds of general formulas (II) and (fIb) can be obtained analoguous by methods known from literature (for example W02006/127426). Scheme 1 R R 2 -'' R

NH

2 2 solvent 3 H HN CI 3 /R5 R R R R 4 4R R (VIII) (IX) R R R 7 R R R R 7 R solvent, base, heat N N N N R3 / H R3 / 5 R 4 (11b) R 10 As depicted in scheme 1, the reaction of an appropriately substituted benzylamine and an appro priately substituted 2-chloroethyl isocyanate (e.g. in 1,4-dioxane or dichloromethane) yielded the appropriately substituted 1-benzyl-3-(2-chloroethyl)urea, which after heating with a base (e.g. NaOH, H 2 0, 1,4-dioxan or diaza(1,3)bicyclo[5.4.0]undecane (DBU), acetonitrile) yielded the appropriately substituted benzyl 1,3-oxazinyl amine (Ilb), or (II) if (VIII) is a racemic mixture of 15 appropriately substituted benzylamines. These methods are generally known to those skilled in the art (WO 2006/127426, pages 22, 26; W02005/063724 page 56, and literature cited therein) The novel substituted compounds of the formula (1) or (Ib) in which R' is -C(O)R'" or -C(O)OR'" and R is hydrogen are obtained when WO 2008/119511 PCT/EP2008/002475 - 19 a compound of formula (II) or (Ib)

R

1 R O R R 9 R1 R R 7 O R9 R 2 R2 N N R'N N 3 / SH 3 / H R R R R R4 II)4 (11b) and a compound of formula (V)

X-C(O)R'

0 or X-C(O)ORO (V) 5 in which R1 0 and R" are as defined above and X is a leaving group as halogen or a compound of formula (VI)

O(-C(O)R'

0

)

2 (VI) are reacted under basic conditions in an aprotic solvent. These reactions are generally known to a person skilled in the art. (See WO 2006/127426, page 23 10 and 32). The compounds of formula (VI) are generally known and commercially available. Scheme 2 R1 R 1 R O R9 R 2 .., 0 3N s N +o 5 HHR R R 0 R R4 (11b) (VI) R R R 7 O0 2 R R solvent, base NN

R

3 / R4 R 1 0

(X)

WO 2008/119511 PCT/EP2008/002475 - 20 Within this type of reaction depicted in scheme 2, organic as well as inorganic bases are useful (e.g. Diisopropylethylamin, Potassiumcarbonate), preferred are aprotic solvents. The reaction tem peratures are between -20 to 40*C, preferred -5*C to 20 0 C. Finally, it has been found that the novel compounds of the formula (I) and (Ib) have pronounced 5 biological properties and are suitable especially for controlling animal pests, in particular insects, arachnids and nematodes encountered in agriculture, in forests, in the protection of stored products and in the protection of materials, and also in the hygiene sector. If appropriate, the compounds of the formula (I) and (Ib) can be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the poly 10 morph mixtures are provided by the invention and can be used according to the invention. The active compounds according to the invention, in combination with good plant tolerance and favourable toxicity to warm-blooded animals and being tolerated well by the environment, are suitable for protecting plants and plant organs, for increasing the harvest yields, for improving the quality of the harvested material and for controlling animal pests, in particular insects, arachnids, 15 helminths, nematodes and molluscs, which are encountered in agriculture, in horticulture, in ani mal husbandry, in forests, in gardens and leisure facilities, in the protection of stored products and of materials, and in the hygiene sector. They may be preferably employed as plant protection agents. They are active against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include: 20 From the order of the Anoplura (Phthiraptera), for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp. From the class of the Arachnida, for example, Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Choriop tes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Erio 25 phyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetrany chus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Poly phagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici. From the class of the Bivalva, for example, Dreissena spp. 30 From the order of the Chilopoda, for example, Geophilus spp., Scutigera spp.

WO 2008/119511 PCT/EP2008/002475 - 21 From the order of the Coleoptera, for example, Acanthoscelides obtectus, Adoretus spp., Agelas tica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., An thonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtec tus, Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., 5 Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, 10 Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Popillia japonica, Premnotrypes spp., Psylliodes chryso cephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp. 15 From the order of the Collembola, for example, Onychiurus armatus. From the order of the Dermaptera, for example, Forficula auricularia. From the order of the Diplopoda, for example, Blaniulus guttulatus. From the order of the Diptera, for example, Aedes spp., Anopheles spp., Bibio hortulanus, Cal liphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia anthro 20 pophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fannia spp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp. From the class of the Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Dero 25 ceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp. From the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granu 30 losus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Het erakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagosto mum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schisto- WO 2008/119511 PCT/EP2008/002475 - 22 somen spp., Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp., Taenia sagi nata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti. It is furthermore possible to control protozoa, such as Eimeria. 5 From the order of the Heteroptera, for example, Anasa tristis, Antestiopsis spp., Blissus spp., Calo coris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., Helio peltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., 10 Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp. From the order of the Homoptera, for example, Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus 15 spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis 20 spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sac chari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, 25 Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Pere grinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pin naspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gi 30 gas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis grami num, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala fes tina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii.

WO 2008/119511 PCT/EP2008/002475 -23 From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber. 5 From the order of the Isoptera, for example, Reticulitermes spp., Odontotermes spp. From the order of the Lepidoptera, for example, Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus pini arius, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias insulana, Ephestia 10 kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, Laphygma spp., Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., 15 Plutella xylostella, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp. From the order of the Orthoptera, for example, Acheta domesticus, Blatta orientalis, Blattella ger manica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta ameri 20 cana, Schistocerca gregaria. From the order of the Siphonaptera, for example, Ceratophyllus spp., Xenopsylla cheopis. From the order of the Symphyla, for example, Scutigerella immaculata. From the order of the Thysanoptera, for example, Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips 25 cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp. From the order of the Thysanura, for example, Lepisma saccharina. The phytoparasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Be lonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, 30 Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus WO 2008/119511 PCT/EP2008/002475 - 24 semipenetrans, Xiphinema spp. If appropriate, the active compounds according to the invention can, at certain concentrations or application rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (in 5 cluding agents against viroids) or as agents against MLO (Mycoplasma-like organisms) and RLO (Rickettsia-like organisms). If appropriate, they can also be employed as intermediates or precur sors for the synthesis of other active compounds. The active compounds can be converted to the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble 10 granules, granules for broadcasting, suspension-emulsion concentrates, natural materials impregnated with active compound, synthetic materials impregnated with active compound, fertilizers and micro encapsulations in polymeric substances. These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that 15 is emulsifiers and/or dispersants and/or foam-formers. The formulations are prepared either in suit able plants or else before or during the application. Suitable for use as auxiliaries are substances which are suitable for imparting to the active com pounds itself and/or to preparations derived therefrom (for example spray liquors, seed dressings) particular properties such as certain technical properties and/or also particular biological proper 20 ties. Typical suitable auxiliaries are: extenders, solvents and carriers. Suitable extenders are, for example, water, polar and non-polar organic chemical liquids, for ex ample from the classes of the aromatic and non-aromatic hydrocarbons (such as paraffins, alkyl benzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, if appropriate, may also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexa 25 none), esters (including fats and oils) and (poly)ethers, the unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide). If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphtha 30 lenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloro ethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffms, for exam ple petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and also their WO 2008/119511 PCT/EP2008/002475 -25 ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexa none, strongly polar solvents such as dimethyl sulphoxide, and also water. Suitable solid carriers are: for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, 5 attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-formers are: for ex 10 ample, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, aryl sulphonates and also protein hydrolysates; suitable dispersants are nonionic and/or ionic substances, for example from the classes of the alcohol-POE and/or -POP ethers, acid and/or POP-POE esters, alkyl aryl and/or POP-POE ethers, fat and/or POP-POE adducts, POE- and/or POP-polyol deriva 15 tives, POE- and/or POP-sorbitan- or -sugar adducts, alkyl or aryl sulphates, alkyl- or arylsulpho nates and alkyl or aryl phosphates or the corresponding PO-ether adducts. Furthermore, suitable oligo- or polymers, for example those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly)alcohols or (poly)amines. It is also possible to employ lignin and its sulphonic acid derivatives, unmodified and modified celluloses, 20 aromatic and/or aliphatic sulphonic acids and their adducts with formaldehyde. Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of pow ders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natu ral phospholipids such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. 25 It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocya nine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybde num and zinc. Other possible additives are perfumes, mineral or vegetable, optionally modified oils, waxes and 30 nutrients (including trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, mo lybdenum and zinc. Stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or WO 2008/119511 PCT/EP2008/002475 -26 other agents which improve chemical and/or physical stability may also be present. The formulations generally comprise between 0.01 and 98% by weight of active compound, prefera bly between 0.5 and 90%. The active compound according to the invention can be used in its commercially available formula 5 tions and in the use forms, prepared from these formulations, as a mixture with other active com pounds, such as insecticides, attractants, sterilizing agents, bactericides, acaricides, nematicides, fun gicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals. Particularly favourable mixing components are, for example, the following compounds: Fungicides: 10 Inhibitors of nucleic acid synthesis benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimol, ethirimol, furalaxyl, hy mexazol, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid Inhibitors of mitosis and cell division benomyl, carbendazim, diethofencarb, fuberidazole, pencycuron, thiabendazole, thiophanat-methyl, 15 zoxamide Inhibitors of respiratory chain complex I diflumetorim Inhibitors of respiratory chain complex II boscalid, carboxin, fenfuram, flutolanil, furametpyr, mepronil, oxycarboxin, penthiopyrad, thif 20 luzamide Inhibitors of respiratory chain complex III azoxystrobin, cyazofamid, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, pyraclostrobin, picoxystrobin Decouplers 25 dinocap, fluazinam WO 2008/119511 PCT/EP2008/002475 - 27 Inhibitors of ATP production fentin acetate, fentin chloride, fentin hydroxide, silthiofam Inhibitors of amino acid biosynthesis and protein biosynthesis andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, 5 pyrimethanil Inhibitors of signal transduction fenpiclonil, fludioxonil, quinoxyfen Inhibitors of lipid and membrane synthesis chlozolinate, iprodione, procymidone, vinclozolin 10 ampropylfos, potassium-ampropylfos, edifenphos, iprobenfos (IBP), isoprothiolane, pyrazophos tolclofos-methyl, biphenyl iodocarb, propamocarb, propamocarb hydrochloride Inhibitors of ergosterol biosynthesis fenhexamid, 15 azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, dinicona zole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flu triafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, my clobutanil, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebucona zole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, voriconazole, imazalil, ima 20 zalil sulphate, oxpoconazole, fenarimol, flurprimidole, nuarimol, pyrifenox, triforine, pefurazoate, prochloraz, triflumizole, viniconazole, aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, spiroxamine, naftifme, pyributicarb, terbinafme Inhibitors of cell wall synthesis WO 2008/119511 PCT/EP2008/002475 -28 benthiavalicarb, bialaphos, dimethomorph, flumorph, iprovalicarb, polyoxins, polyoxorim, validamy cin A Inhibitors of melanin biosynthesis capropamid, diclocymet, fenoxanil, phthalid, pyroquilon, tricyclazole 5 Resistance inductors acibenzolar-S-methyl, probenazole, tiadinil Multisite captafol, captan, chlorothalonil, copper salts such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture, dichlofluanid, di 10 thianon, dodine, dodine free base, ferbam, folpet, fluorofolpet, guazatine, guazatine acetate, iminoc tadine, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, propineb, sulphur and sulphur preparations containing calcium polysulphide, thiram, tolylfluanid, zineb, ziram Unknown mechanism 15 amibromdol, benthiazol, bethoxazin, capsimycin, carvone, chinomethionat, chloropicrin, cufraneb, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, dichlorophen, dicloran, difenzoquat, difenzoquat methyl sulphate, diphenylamine, ethaboxam, ferinizone, flumetover, flusulphamide, flu opicolide, fluoroimide, hexachlorobenzene, 8-hydroxyquinoline sulphate, irumamycin, methasulpho carb, metrafenone, methyl isothiocyanate, mildiomycin, natamycin, nickel dimethyl dithiocarbamate, 20 nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts, 2 phenylphenol and salts, piperalin, propanosine-sodium, proquinazid, pyrrol nitrin, quintozene, te cloftalam, tecnazene, triazoxide, trichlamide, zarilamid and 2,3,5,6-tetrachloro-4 (methylsulphonyl)pyridine, N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulphonamide, 2 amino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden 25 4-yl)-3-pyridinecarboxamide, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine, cis-1-(4 chlorophenyl)-2-(lH-1,2,4-triazol-1-yl)cycloheptanol, 2,4-dihydro-5-methoxy-2-methyl-4-[[[[1-[3 (trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,3-triazol-3-one (185336-79-2), methyl 1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate, 3,4,5-trichloro-2,6 pyridinedicarbonitrile, methyl 2-[[[cyclopropyl[(4-methoxyphenyl)imino]methyl]thio]methyl]-alpha.

30 (methoxymethylene)benzacetate, 4-chloro-alpha-propynyloxy-N-[2-[3-methoxy-4-(2 propynyloxy)phenyl]ethyl]benzacetamide, (2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3- WO 2008/119511 PCT/EP2008/002475 -29 methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]butanamide, 5-chloro-7-(4 methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6 trifluorophenyl)-N-[(1R)-1,2,2-trimethylpropyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine, 5-chloro-N [(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, N-[1-(5 5 bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide, N-(5-bromo-3-chloropyridin-2 yl)methyl-2,4-dichloronicotinamide, 2-butoxy-6-iodo-3-propylbenzopyranon-4-one, N-{(Z) [(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-benzacetamide, N (3-ethyl-3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxybenzamide, 2-[[[[1-[3(1 -fluoro-2 phenylethyl)oxy]phenyl]ethylidene]amino]oxy]methyl]-alpha-(methoxyimino)-N-methyl-alphaE 10 benzacetamide, N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide, N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-iH-pyrazole-4-carboxamide, N (6-methoxy-3-pyridinyl)cyclopropanecarboxamide, 1-[(4-methoxyphenoxy)methyl]-2,2 dimethylpropyl-lH-imidazole-1-carboxylic acid, 0-[i-[(4-methoxyphenoxy)methyl]-2,2 dimethylpropyl]-lH-imidazole-1-carbothioic acid, 2-(2-{[6-(3-chloro-2-methylphenoxy)-5 15 fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide Bactericides: bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations. 20 Insecticides/acaricides/nematicides: Acetylcholine esterase (AChE) inhibitors carbamates, for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulphan, cloetho 25 carb, dimetilan, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thio dicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate organophosphates, for example acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos 30 (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlor mephos, chlorpyrifos (-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, WO 2008/119511 PCT/EP2008/002475 -30 demeton-S-methyl, demeton-S-methylsulphone, dialifos, diazinon, dichlofenthion, dichlor vos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulphoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulphothion, fenthion, flupyrazofos, fonofos, formothion, fosmethilan, fosthiazate, heptenophos, iodofenphos, iprobenfos, isazofos, 5 isofenphos, isopropyl O-salicylate, isoxathion, malathion, mecarbam, methacrifos, methamido phos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion (-methyl/-ethyl), phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl/-ethyl), profenofos, propaphos, propetamphos, prothiofos, prothoate, pyraclofos, pyri 10 daphenthion, pyridathion, quinalphos, sebufos, sulphotep, sulprofos, tebupirimfos, temephos, ter bufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, vamidothion Sodium channel modulators / voltage-dependent sodium channel blockers pyrethroids, for example acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, 15 bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyflu thrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, deltamethrin, empen thrin (IR isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma 20 cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis-, trans-), phenothrin (1R-trans-isomer), prallethrin, profluthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (lR isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrins (pyrethrum) DDT 25 oxadiazines, for example indoxacarb semicarbazones, for example metaflumizone (BAS3201) Acetylcholine receptor agonists/antagonists 30 chloronicotinyls, WO 2008/119511 PCT/EP2008/002475 -31 for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiaclo prid, imidaclothiz, AKD-1022, thiamethoxam nicotine, bensultap, cartap Acetylcholine receptor modulators 5 spinosyns, for example spinosad, spinetoram (XDE- 175) GABA-controlled chloride channel antagonists organochlorines, for example camphechlor, chlordane, endosulphan, gamma-HCH, HCH, heptachlor, lindane, meth 10 oxychlor fiprols, for example acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole Chloride channel activators mectins, 15 for example abarmectin, emamectin, emamectin-benzoate, ivermectin, lepimectin, milbemycin Juvenile hormone mimetics, for example diofenolan, epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxifen, triprene Ecdysone agonists/disruptors 20 diacylhydrazines, for example chromafenozide, halofenozide, methoxyfenozide, tebufenozide Chitin biosynthesis inhibitors benzoylureas, for example bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, WO 2008/119511 PCT/EP2008/002475 - 32 hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron buprofezin cyromazine Oxidative phosphorylation inhibitors, ATP disruptors 5 diafenthiuron organotin compounds, for example azocyclotin, cyhexatin, fenbutatin-oxide Oxidative phosphorylation decouplers acting by interrupting the H-proton gradient pyrroles, 10 for example chlorfenapyr dinitrophenols, for example binapacyrl, dinobuton, dinocap, DNOC Site-I electron transport inhibitors METIs, 15 for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad hydramethylnon dicofol Site-fl electron transport inhibitors rotenone 20 Site-rI electron transport inhibitors acequinocyl, fluacrypyrim Microbial disruptors of the insect gut membrane WO 2008/119511 PCT/EP2008/002475 - 33 Bacillus thuringiensis strains Lipid synthesis inhibitors tetronic acids, for example spirodiclofen, spiromesifen 5 tetramic acids, for example spirotetramat carboxamides, for example flonicamid octopaminergic agonists, 10 for example amitraz Inhibitors of magnesium-stimulated ATPase, propargite nereistoxin analogues, for example thiocyclam hydrogen oxalate, thiosultap-sodium 15 Ryanodin receptor agonists benzoic acid dicarboxamides, for example flubendiamid anthronilamides, for example pynaxypyr (3-bromo-N-{4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl}-1-(3 20 chloropyridin-2-yl)-1H-pyrazole-5-carboxamide) Biologicals, hormones or pheromones azadirachtin, Bacillus spec., Beauveria spec., codlemone, Metarrhizium spec., Paecilomyces spec., thuringiensin, Verticillium spec.

WO 2008/119511 PCT/EP2008/002475 - 34 Active compounds with unknown or unspecific mechanisms of action fumigants, for example aluminium phosphide, methyl bromide, sulphuryl fluoride antifeedants, 5 for example cryolite, flonicamid, pymetrozine mite growth inhibitors, for example clofentezine, etoxazole, hexythiazox amidoflumet, benclothiaz, benzoximate, bifenazate, bromopropylate, buprofezin, chinome thionat, chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, cyflumetofen, 10 dicyclanil, fenoxacrim, fentrifanil, flubenzimine, flufenerim, flutenzin, gossyplure, hydramethyl none, japonilure, metoxadiazone, petroleum, piperonyl butoxide, potassium oleate, pyridalyl, sul phluramid, tetradifon, tetrasul, triarathene, verbutin A mixture with other known active compounds, such as herbicides, fertilizers, growth regulators, safeners, semiochemicals, or else with agents for improving the plant properties, is also possible. 15 When used as insecticides, the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergists. Synergists are compounds which increase the action of the active compounds, without it being necessary for the synergistic agent added to be active itself. When used as insecticides, the active compounds according to the invention can furthermore be 20 present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with inhibitors which reduce degradation of the active compound after use in the environment of the plant, on the surface of parts of plants or in plant tissues. The active compound content of the use forms prepared from the commercially available formula tions can vary within wide limits. The active compound concentration of the use forms can be from 25 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1% by weight. The active compounds are employed in a customary manner appropriate for the use forms. All plants and plant parts can be treated in accordance with the invention. Plants are to be under stood as meaning in the present context all plants and plant populations such as desired and unde- WO 2008/119511 PCT/EP2008/002475 - 35 sired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional plant breeding and optimization methods or by bio technological and genetic engineering methods or by combinations of these methods, including the transgenic plants and including the plant cultivars protectable or not protectable by plant breeders' 5 rights. Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. The plant parts also include harvested material, and vegetative and generative propagation material, for ex ample cuttings, tubers, rhizomes, offshoots and seeds. 10 Treatment according to the invention of the plants and plant parts with the active compounds is carried out directly or by allowing the compounds to act on the surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fog ging, scattering, painting on, injection and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats. 15 The active compounds according to the invention are particularly suitable for treating seed. Here, the active compounds according to the invention mentioned above as preferred or particularly pre ferred may be mentioned as being preferred. Thus, a large part of the damage to crop plants which is caused by pests occurs as early as when the seed is attacked during storage and after the seed is introduced into the soil, during and immediately after germination of the plants. This phase is par 20 ticularly critical since the roots and shoots of the growing plant are particularly sensitive and even minor damage can lead to the death of the whole plant. Protecting the seed and the germinating plant by the use of suitable active compounds is therefore of particularly great interest. The control of pests by treating the seeds of plants has been known for a long time and is the sub ject of continuous improvements. However, the treatment of seed entails a series of problems 25 which cannot always be solved in a satisfactory manner. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which dispense with the additional application of crop protection agents after sowing or after the emergence of the plants. It is furthermore desirable to optimize the amount of active compound employed in such a way as to provide maximum pro tection for the seed and the germinating plant from attack by pests, but without damaging the plant 30 itself by the active compound employed. In particular, methods for the treatment of seed should also take into consideration the intrinsic insecticidal properties of transgenic plants in order to achieve optimum protection of the seed and the germinating plant with a minimum of crop protec tion agents being employed.

WO 2008/119511 PCT/EP2008/002475 -36 The present invention therefore in particular also relates to a method for the protection of seed and germinating plants from attack by pests, by treating the seed with an active compound according to the invention. The invention likewise relates to the use of the active compounds according to the invention for the treatment of seed for protecting the seed and the resultant plant from pests. Fur 5 thermore, the invention relates to seed which has been treated with an active compound according to the invention so as to afford protection from pests. One of the advantages of the present invention is that the particular systemic properties of the ac tive compounds according to the invention mean that treatment of the seed with these active com pounds not only protects the seed itself, but also the resulting plants after emergence, from pests. 10 In this manner, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed with. Furthermore, it must be considered as advantageous that the active compounds according to the invention can also be employed in particular in transgenic seed, the plants arising from this seed being capable of expressing a protein directed against pests. By treating such seed with the active 15 compounds according to the invention, certain pests can be controlled merely by the expression of the, for example, insecticidal protein, and additionally be protected by the active compounds ac cording to the invention against damage. The active compounds according to the invention are suitable for protecting seed of any plant vari ety as already mentioned above which is employed in agriculture, in the greenhouse, in forests or 20 in horticulture. In particular, this takes the form of seed of maize, peanut, canola, oilseed rape, poppy, soya beans, cotton, beet (for example sugar beet and fodder beet), rice, sorghum and millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables (for example tomatoes, cab bage plants). The active compounds according to the invention are likewise suitable for treating the seed of fruit plants and vegetables as already mentioned above. The treatment of the seed of 25 maize, soya beans, cotton, wheat and canola or oilseed rape is of particular importance. As already mentioned above, the treatment of transgenic seed with an active compound according to the invention is also of particular importance. This takes the form of seed of plants which, as a rule, comprise at least one heterologous gene which governs the expression of a polypeptide with in particular insecticidal properties. In this context, the heterologous genes in transgenic seed may 30 be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Tricho derma, Clavibacter, Glomus or Gliocladium. The present invention is particularly suitable for the treatment of transgenic seed which comprises at least one heterologous gene orignating from Ba cillus sp. and whose gene product shows activity against the European corn borer and/or the corn WO 2008/119511 PCT/EP2008/002475 - 37 root worm. It is particularly preferably a heterologous gene derived from Bacillus thuringiensis. In the context of the present invention, the active compound according to the invention is applied to the seed either alone or in a suitable formulation. Preferably, the seed is treated in a state which is stable enough to avoid damage during treatment. In general, the seed may be treated at any point 5 in time between harvest and sowing. The seed usually used has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. When treating the seed, care must generally be taken that the amount of the active compound ac cording to the invention applied to the seed and/or the amount of further additives is chosen in such a way that the germination of the seed is not adversely affected, or that the resulting plant is 10 not damaged. This must be borne in mind in particular in the case of active compounds which may have phytotoxic effects at certain application rates. As already mentioned above, it is possible to treat all plants and their parts according to the inven tion. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by con ventional biological breeding methods, such as crossing or protoplast fusion, and parts thereof, are 15 treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by ge netic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The terms "parts", "parts of plants" and "plant parts" have been explained above. Particularly preferably, plants of the plant cultivars which are in each case commercially available 20 or in use are treated according to the invention. Plant cultivars are to be understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, bio- or genotypes. Depending on the plant species or plant cultivars, their location and growth conditions (soils, cli mate, vegetation period, diet), the treatment according to the invention may also result in superad 25 ditive ("synergistic") effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the active compounds and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flower ing performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality 30 and/or a higher nutritional value of the harvested products, better storage stability and/or proc essability of the harvested products are possible, which exceed the effects which were actually to be expected.

WO 2008/119511 PCT/EP2008/002475 -38 The transgenic plants or plant cultivars (obtained by genetic engineering) which are preferably to be treated according to the invention include all plants which, by virtue of the genetic modifica tion, received genetic material which imparted particularly advantageous, useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low tempera 5 tures, increased tolerance to drought or to water or soil salt content, increased flowering perform ance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further and particularly emphasized examples of such traits are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopa 10 thogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbi cidally active compounds. Examples of transgenic plants which may be mentioned are the impor tant crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, 15 potatoes, cotton, tobacco and oilseed rape. Traits that are emphasized are in particular increased defence of the plants against insects, arachnids, nematodes and slugs and snails by virtue of toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CryLA(a), CryIA(b), CryIA(c), CrylIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (referred to hereinbelow as "Bt 20 plants"). Traits that are also particularly emphasized are the increased defence of the plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are further more particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for ex 25 ample the "PAT" gene). The genes which impart the desired traits in question can also be present in combination with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD@ (for example maize, cotton, soya beans), KnockOut® (for example maize), StarLink® (for example maize), Bollgard@ (cotton), Nucotn@ (cotton) and 30 NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready@ (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link@ (tolerance to phosphinotricin, for example oilseed rape), IMI@ (tolerance to imidazolinones) and STS@ (tol erance to sulphonylureas, for example maize). Herbicide-resistant plants (plants bred in a conven 35 tional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield@ (for example maize). Of course, these statements also apply to plant cultivars WO 2008/119511 PCT/EP2008/002475 -39 having these genetic traits or genetic traits still to be developed, which plant cultivars will be de veloped and/or marketed in the future. The plants listed can be treated according to the invention in a particularly advantageous manner with the active compounds of the general formula I according to the invention. The preferred 5 ranges stated above for the active compounds also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the active compounds specifically mentioned in the present text. The active compounds according to the invention act not only against plant, hygiene and stored product pests, but also in the veterinary medicine sector against animal parasites (ecto- and 10 endoparasites), such as hard ticks, soft ticks, mange mites, leaf mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, feather lice and fleas. These parasites include: From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp. From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example, 15 Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp. From the order of the Diptera and the suborders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lut zomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haema 20 topota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haemato bia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp. From the order of the Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla 25 spp., Ceratophyllus spp. From the order of the Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., Pan strongylus spp. From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.

WO 2008/119511 PCT/EP2008/002475 - 40 From the subclass of the Acari (Acarina) and the orders of the Meta- and Mesostigmata, for exam ple, Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp. 5 From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp. 10 The active compounds of the formula (I) according to the invention are also suitable for control ling arthropods which infest agricultural productive livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese and bees, other pets, such as, for example, dogs, cats, caged birds and aquarium fish, and also so-called test animals, such as, for example, hamsters, guinea pigs, rats and mice. By controlling these arthro 15 pods, cases of death and reduction in productivity (for meat, milk, wool, hides, eggs, honey etc.) should be diminished, so that more economic and easier animal husbandry is possible by use of the active compounds according to the invention. The active compounds according to the invention are used in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, cap 20 sules, potions, drenches, granules, pastes, boluses, the feed-through process and suppositories, by parenteral administration, such as, for example, by injection (intramuscular, subcutaneous, intra venous, intraperitoneal and the like), implants, by nasal administration, by dermal use in the form, for example, of dipping or bathing, spraying, pouring on and spotting on, washing and powdering, and also with the aid of moulded articles containing the active compound, such as collars, ear 25 marks, tail marks, limb bands, halters, marking devices and the like. When used for cattle, poultry, pets and the like, the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, free-flowing compositions), which com prise the active compounds in an amount of 1 to 80% by weight, directly or after 100 to 10 000 fold dilution, or they can be used as a chemical bath. 30 It has furthermore been found that the active compounds according to the invention also have a strong insecticidal action against insects which destroy industrial materials.

WO 2008/119511 PCT/EP2008/002475 -41 The following insects may be mentioned as examples and as preferred - but without any limitation: Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium ru fovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon 5 aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus; Hymenopterons, such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur; Termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticuliter mes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, 10 Zootermopsis nevadensis, Coptotermes formosanus; Bristletails, such as Lepisma saccharina. Industrial materials in the present connection are to be understood as meaning non-living materi als, such as, preferably, plastics, adhesives, sizes, papers and cardboards, leather, wood and proc essed wood products and coating compositions. 15 The ready-to-use compositions may, if appropriate, comprise further insecticides and, if appropri ate, one or more fungicides. With respect to possible additional additives, reference may be made to the insecticides and fungi cides mentioned above. The active compounds according to the invention can likewise be employed for protecting objects 20 which come into contact with seawater or brackish water, such as hulls, screens, nets, buildings, moorings and signalling systems, against fouling. Furthermore, the active compounds according to the invention, alone or in combinations with other active compounds, may be employed as antifouling agents. In domestic, hygiene and stored-product protection, the active compounds are also suitable for 25 controlling animal pests, in particular insects, arachnids and mites, which are found in enclosed spaces such as, for example, dwellings, factory halls, offices, vehicle cabins and the like. They can be employed alone or in combination with other active compounds and auxiliaries in domestic insecticide products for controlling these pests. They are active against sensitive and resistant spe cies and against all developmental stages. These pests include: WO 2008/119511 PCT/EP2008/002475 -42 From the order of the Scorpionidea, for example, Buthus occitanus. From the order of the Acarina, for example, Argas persicus, Argas reflexus, Bryobia ssp., Derma nyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trom bicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermato 5 phagoides forinae. From the order of the Araneae, for example, Aviculariidae, Araneidae. From the order of the Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium. From the order of the Isopoda, for example, Oniscus asellus, Porcellio scaber. 10 From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus spp. From the order of the Chilopoda, for example, Geophilus spp. From the order of the Zygentoma, for example, Ctenolepisma spp., Lepisma saccharina, Lepis modes inquilinus. From the order of the Blattaria, for example, Blatta orientalies, Blattella germanica, Blattella asahi 15 nai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa. From the order of the Saltatoria, for example, Acheta domesticus. From the order of the Dermaptera, for example, Forficula auricularia. From the order of the Isoptera, for example, Kalotermes spp., Reticulitermes spp. 20 From the order of the Psocoptera, for example, Lepinatus spp., Liposcelis spp. From the order of the Coleoptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophi lus oryzae, Sitophilus zeamais, Stegobium paniceum. From the order of the Diptera, for example, Aedes aegypti, Aedes albopictus, Aedes taeniorhyn 25 chus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.

WO 2008/119511 PCT/EP2008/002475 -43 From the order of the Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia inter punctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella. From the order of the Siphonaptera, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis. 5 From the order of the Hymenoptera, for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum. From the order of the Anoplura, for example, Pediculus humanus capitis, Pediculus humanus cor poris, Pemphigus spp., Phylloera vastatrix, Phthirus pubis. From the order of the Heteroptera, for example, Cimex hemipterus, Cimex lectularius, Rhodinus 10 prolixus, Triatoma infestans. In the field of household insecticides, the active compounds according to the invention are used alone or in combination with other suitable active compounds, such as phosphoric esters, car bamates, pyrethroids, neonicotinoids, growth regulators or active compounds from other known classes of insecticides. 15 The active compounds according to the invention are used in aerosols, pressure-free spray prod ucts, for example pump and atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or polymer, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free, or passive, evaporation sys tems, moth papers, moth bags and moth gels, as granules or dusts, in baits for spreading or in bait 20 stations.

WO 2008/119511 PCT/EP2008/002475 - 44 Preparation Examples: Process 1 (2Z)-2-{[1-(2-chlorophenyl)ethyl]imino}-N-(2-methoxyethyl)-1,3-oxazolidine-3-carbothioamide ci N H N Compound (10) 5 400 mg (1.78 mmol) N-[1-(2-chlorophenyl)ethyl]-4,5-dihydro-1,3-oxazol-2-amine were initially charged in 10 ml dichloromethane with 209 mg (1.78 mmol) methoxyethylisothiocyanate and sub sequently, 214 mg (1.66 mmol) N,N-diisopropylethylamine, solved in 1 ml dichlormethane, were added tropwise. The reaction mixture was stirred 15 h at 20*C and finally all volatile ingredients were evaporated. The reaction gave 600 mg (99 % of theory) of compound 10. Log P acidic 4.08, 10 1H-NMR (CDCl 3 ) q 5.24 ppm. CI CI NiPr2Et O + '_-0 ' NCS N=< / N D HN HN _O This procedure can be employed analogously for all compounds of formula (I) in which R 8 is C(S)NR"R , and R1 2 is hydrogen. If the oxazole-amine is present as chiral compound according to formula (Ib), this procedure can be employed analogously for all compounds of formula (Ib) in 15 which R 8 is -C(S)NR"R1 2 , and R1 2 is hydrogen.

WO 2008/119511 PCT/EP2008/002475 -45 Process 2 (2Z)-N-(cyanomethyl)-2-[(1-phenylethyl)imino]-1,3-oxazolidine-3-carbothioamide O N zz H N

N

/, S N Compound (94*) 200 mg (1.05 mmol) N-[(IS)-1-phenylethyl]-4,5-dihydro-1,3-oxazol-2-amine and 206 mg (1.16 5 mmol) thiocarbonyldiimidazol were stirred in 40 ml dichloromethane for 1 2 h at room tempera ture. Subsequently, 65 mg (1.16 mmol) aminoacetonitrile were added and the mixture was further stirred for 15 h at room temperature. For processing, water was added, the organic phase was re moved, dried with sodium sulfate, filtered, and solvents were removed. The product obtained was purified by column chromatography with dichloromethane on aluminium oxide and 50 mg (16 % 10 of theory) of compound 94* were thus isolated. LogP acidic 3.07, 1H-NMR (DMSO-d6) q 4.78 ppm. N N O H O + O\N N + NH 2 S N / S N This procedure can be employed analogously for all compounds of formula (Ib) in which R 8 is C(S)NR"R 2 , and R1 2 is hydrogen or alkyl. If the oxazole-amine is present as racemic mixture ac 15 cording to formula (II), this procedure can be employed analogously for all compounds of formula (I) in which R 8 is -C(S)NR"R 2 , and R1 2 is hydrogen or alkyl. Further compounds of the formula (I) and (Ib) are listed in Table 1 below.

WO 2008/119511 PCT/EP2008/002475 - 46 N00 00 0 0)0 00 z I U) 0 o o cn co co~,o o- z WO 2008/119511 PCT/EP2008/002475 - 47 %0 en -1 r r- CI m' 1:T QUO tn in 0 k n o N)C4r - 00 00 00 w m N ' kO0 n m 0 ~ 0 0 0 0 C U CI In CtI cn c) co) c) V) Cd) U) U) cd) cd CI) Cd) cd) cd) cd) cd) O00 -C4 in O 00 a,\0 C) l cn It in 10 U ~O N 00 C - - - - - .- .- q . . .l .l .lC l WO 2008/119511 PCT/EP2008/002475 - 48 ~ t00 W) 0'. 00 m 0 ~O ft '.f C ' C'. " '.O tn 0'. 0 m %OO Cl) 0 0 LL 00 0 0 . u u u 0 P C/) C,) U) d d d C) C~ d o re 00 C'. 0) M- Cl 1/'. r- 00 0'. Q C4 " C4 en n Cf. M~ C". ff. C". m" en WO 2008/119511 PCT/EP2008/002475 - 49 N) ON N0 cq ON V 0 00 0 z z z z z z Cl) () Cl) UI) C/)C) 'C) (4) Q WO 2008/119511 PCT/EP2008/002475 50 u uu 0 cs10 C-) z z z z z z 00 C C)COC C U I-NT k) k o WO 2008/119511 PCT/EP2008/002475 51 5' 5' 5' 5'55 CA 03 w" C4 kn 00 Ln 00 ~ r-*:1 00 0 Cl) 0 U)U z z z z U) U) Cl) U) ~ 'U) IT 0n r0 00 C\ 0) WO 2008/119511 PCT/EP2008/002475 52 0 0U IL LL I~~ M z z z z z z C/) C/) UI) Cl) l) C) U 4~ WO 2008/119511 PCT/EP2008/002475 53 00 c

U,

U)U) U)U)U) CO. 00LL U N N WO 2008/119511 PCT/EP2008/002475 54 -. l )0 - WI) kn Cl 00 00 m~ C4 IL L Ilk u Q 0KL U)~~~ u)~ U )Q ZN0 u u U) C/) U) U U o e 1r~ N00 ' U Z r NN WO 2008/119511 PCT/EP2008/002475 55 0 0 -. ~ - - N -~ 0 001 t~ 0 " 0O 0 C.. Z I I~ u QQ UA 0 u O U L) QC zz UUU) UQU U Cj) -/ C14 M/ It) C/) C/) r'- M C', ) 2 Z ' U 00 0000 00w00000 wN mONmm C C ON 'O WO 2008/119511 PCT/EP2008/002475 56 of) u ~ u uuu uuu C4 u u u uuuu uuuI Z 0I _: m T I- _n _l w C71, C C/ fI C ) C/) C) C/) C) C) C) C) C) Cd) C') C') / WO 2008/119511 PCT/EP2008/002475 57 C4 C C 0 0 0 0 o= 0~ ZZ mZI zmZI C 0 2 l Znr WO 2008/119511 PCT/EP2008/002475 58 jm Vmz 000 WO 2008/119511 PCT/EP2008/002475 59 000 0r S0 < 0 Z ZI: ZI U u uN WO 2008/119511 PCT/EP2008/002475 60 o o ZI ZI ZI0 o o o o WO 2008/119511 PCT/EP2008/002475 61 u I WO 2008/119511 PCT/EP2008/002475 62 0'm 0'0'0' NZ Nmz _ _ _ _ U, , U 00 CC WO 2008/119511 PCT/EP2008/002475 63 UC-) It- - 00 CA) cc) C, C-5) K0

ZIZ

WO 2008/119511 PCT/EP2008/002475 64 ju 00 mz z 71 z ZI: * ) * * ;L 4-4 2c o ei WO 2008/119511 PCT/EP2008/002475 65 0 0> 00 00 ~ _ 1rzt:i Izm 5 * * * * kn n k WO 2008/119511 PCT/EP2008/002475 66 .~ ~u C,)) :ZFI

U

U)

* ** 00 0 2 2 2 0 0 WO 2008/119511 PCT/EP2008/002475 67 00 00 irn 00 U) IN~U WO 2008/119511 PCT/EP2008/002475 68 NN _ 0 0N 00 Qz z= I-I:Z I 0L 00 WO 2008/119511 PCT/EP2008/002475 69 00 O )O zz KZ K>, <>: K

*

WO 2008/119511 PCT/EP2008/002475 70 LjLL MI U- U zm:LL

L

000 N N N00 o u WO 2008/119511 PCT/EP2008/002475 71 0 zm 02 00 00 00 o u WO 2008/119511 PCT/EP2008/002475 72 u0 00 /z 0 00 * * 00 00 00 2 000 WO 2008/119511 PCT/EP2008/002475 73 00 00 L 0

ZI

ZI- ZI K: _ UZI ;L4, 00 C WO 2008/119511 PCT/EP2008/002475 74 n Oo C) o I 0. 00 uNO WO 2008/119511 PCT/EP2008/002475 75 U,) Iz <2' Iz ZI LLZI ZI LL U) U ON ONe WO 2008/119511 PCT/EP2008/002475 76 (-' 00 kn kIn cni u~i WO 2008/119511 PCT/EP2008/002475 77 00 000 U) U) Z~IZ LL-U 00 CN C> o D (= WO 2008/119511 PCT/EP2008/002475 78 u 0l enn ZI: ZI: ZI 2Z o oq WO 2008/119511 PCT/EP2008/002475 79 000 enI ZZ: z0 XZI N 000 2q Cl o WO 2008/119511 PCT/EP2008/002475 80 ND co 0) 00 ij t C,,z ZI: ZI O 2; 5z 5 Cl l C o o WO 2008/119511 PCT/EP2008/002475 81 (I) U) LL MZ

UU

Co 00 C WO 2008/119511 PCT/EP2008/002475 82 C m MzI 0 Iz 0>: Lz LLL en Cl o WO 2008/119511 PCT/EP2008/002475 83 u u Iu u z T- "0 LL O~(N/ 00, rn en ,n Iz4 'C'4 C1zc uZ WO 2008/119511 PCT/EP2008/002475 84 00 00 Cj) U) U- L z Z LL LL Zx LL

U

LL ;L4 cit a *~:j- WO 2008/119511 PCT/EP2008/002475 85 U. U CD 0 zm: mtz V-4 N 00 o WO 2008/119511 PCT/EP2008/002475 86 00 lV 00 0f Uz U) 0 0 a0 (n N( o 0L.

WO 2008/119511 PCT/EP2008/002475 87 U0' coo Z- ZI .LP LL LLL 0 00 WO 2008/119511 PCT/EP2008/002475 88 ~ C> C') C-)) ~zI ZI i K>) K>) ZZ: U afm 0 2o WO 2008/119511 PCT/EP2008/002475 89 C0 00 kn00 C0t _cl CD U) ZI Z Z 0 ClCl l 4 C11 WO 2008/119511 PCT/EP2008/002475 90 00 00' WO 2008/119511 PCT/EP2008/002475 -91 Preparation of starting materials N-[ 1 -(2-chlorophenyl)ethyl]-4,5-dihydro- 1,3-oxazol-2-amine C 0 N N H Step 1: 3.2 g (20.6mmol) 1-(2-chlorophenyl)ethaneamine [CAS 39959-67-6] and 52.3 g (22.6 mmol) triethylamine were given into 20 ml dichloromethane and afterwards 2.4 g (22.6 mmol) 2 chloroethylisocyanat werde added dropwise. The mixture was allowed to react 15 hours at 20'C. The volatile components were evaporated to give 1-(2-chloroethyl)-3-[1-(2 chlorophenyl)ethyl]urea (log p = 2.3) that was used in step 2 without further purification Step 2: 7.2 g (27.5 mmol) 1-(2-chloroethyl)-3-[1-(2-chlorophenyl)ethyl]urea , 5.25 g (34.5 mmol) 1,8 diazabicyclo(5.4.0)undec-7-en (DBU) were heated to 60 'C in 60 ml of acetonitrile for about 15 hours. The volatile components were evaporated, and the residue was dissolved in water and di chloromethane. The organic phase was dried with sodiumsulfate and after filtration evaporated. The remaining solid was washed with cold acetonitrile to give 2.4 g N-[1-(2-chlorophenyl)ethyl] 4,5-dihydro-1,3-oxazol-2-amine (39 % of theory). (lH-NMR (CDCl3): 4.76 quartett) N-[(I S)-I -phenylethyl]-4,5-dihydro-1,3-oxazol-2-amine N N

H

WO 2008/119511 PCT/EP2008/002475 - 92 Step 1: 6.1 g (50.3 mmol) 1(S)-1-phenylethylamine [CAS 2627-86-3] and 5.6 g (55.3 mmol) triethylamine were given into 45 ml dichloromethane and afterwards 5.8 g (22.6 mmol) 2-chloroethylisocyanate were added dropwise. The mixture was allowed to react 15 hours at 20*C. The volatile compo nents were evaporated to give 1-(2-chloroethyl)-3-[(1 S)-i -phenylethyl]urea (log p = 1.76) that was used in step 2 without further purification. Step 2: 11.4 g (50.3 mmol) 1-(2-chloroethyl)-3-[(1S)-1-phenylethyl]urea, and 9.6 g (63 mmol) 1,8 diazabicyclo(5.4.0)undec-7-en (DBU) were heated to 60*C in 50 ml of acetonitrile for about 15 hours. The volatile components were evaporated; the residue was dissolved in ethyl acetate and washed three times with water. The organic phase was dried with sodiumsulfate and after filtration evaporated to give 8 g N-[(1S)-1-phenylethyl]-4,5-dihydro-1,3-oxazol-2-amine (79 % of theory). (1H-NMR (DMSO-d6): 4.61 quartett) WO 2008/119511 PCT/EP2008/002475 - 93 Biologzical Examples Example No. 1 Myzus test (spray treatment) Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emul sifier-containing water to the desired concentration. Disks of Chinese cabbage (Brassica pekinensis) which are infested with all stages of the green peach aphid (Myzus persicae) are sprayed with a preparation of active compound of the desired concentration. After the desired period of time, the effect in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed. In this test, for example, the following compounds of table 1 show at least 80 % activity at a con centration of 500 g/ha: Compounds No. 1-8, 11-48, 51, 54-57, 59-69, 72, 74, 75, and 77-93.

WO 2008/119511 PCT/EP2008/002475 - 94 Example No. 2 Tetranychus test, OP-resistant (spray treatment) Solvents: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with emul sifier-containing water to the desired concentration. Discs of bean leaves (Phaseolus vulgaris) which are infested by all stages of the greenhouse red spider mite (Tetranychus urticae) are sprayed with a preparation of active compound of the desired concentration. After the desired period of time, the effect in % is determined. 100% means that all spider mites have been killed; 0% means that none of the spider mites have been killed. In this test, for example, the following compounds of table 1 show at least 80 % activity at a con centration of 20 g/ha: Compounds No. 3, 5, 25, 32, and 34. In this test, for example, the following compounds of table 1 show at least 80 % activity at a con centration of 100 g/ha: Compounds No. 2, 11, 15, 20, 21, 22, 24, 28, 33, 35-38, 40-42, 45, 47, and 78. In this test, for example, the following compound of table 1 shows at least 80 % activity at a con centration of 500 g/ha: Compound No. 27.

WO 2008/119511 PCT/EP2008/002475 -95 Example No. 3 Meloidogyne test (spray treatment) Solvent: 80 parts by weight of acetone To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent, and the concentrate is diluted with water to the desired concentration. Containers are filled with sand, active compound solution, Meloidogyne incognita egg/larvae sus pension and lettuce seeds. The lettuce seeds germinate and the plants develop. On the roots, galls are formed. After the desired period of time, the nematicidal activity is determined by the formation of galls in %. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to that of the untreated controls. In this test, for example, the following compounds of table 1 show at least 80 % activity at a con centration of 20 ppm: Compounds No. 62-65.

WO 2008/119511 PCT/EP2008/002475 - 96 Example No. 4 Aphis gossypii test (spray treatment) Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emul sifier-containing water to the desired concentration. Cotton leaves (Gossypium hirsutum) which are heavily infested with the cotton aphid (Aphis gos sypii) are sprayed with a preparation of active compound of the desired concentration. After the desired period of time, the kill in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed. In this test, for example, the following compounds of table 1 show at least 80 % activity at a con centration of 100 ppm: Compounds No. 6-8.

WO 2008/119511 PCT/EP2008/002475 - 97 Example No. 5 Boophilus microplus test (injection) Solvent: dimethyl sulphoxide To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with solvent to the desired concentration. The solution of active compound is injected into the abdomen (Boophilus microplus), and the ani mals are transferred into dishes and kept in a temperature-controlled room. After the desired period of time, the effect in % is determined. 100% means that no tick has laid any fertile eggs. In this test, for example, the following compound of table 1 shows at least 80 % activity at a con centration of 20 ig/animal: Compound No. 78.

WO 2008/119511 PCT/EP2008/002475 -98 Comparative Biological Examples Example No. 1 Myzus test (MYZUPE spray treatment) Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emul sifier-containing water to the desired concentration. Disks of Chinese cabbage (Brassica pekinensis) which are infested with all stages of the green peach aphid (Myzus persicae) are sprayed with a preparation of active compound of the desired concentration. After the desired period of time, the effect in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed. In this test, for example, the following compounds of table 1 show an activity superior to the prior art: see table 2 WO 2008/119511 PCT/EP2008/002475 - 99 Example No. 2 Tetranychus test; OP-resistant (TETRUR spray treatment) Solvents: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with emul sifier-containing water to the desired concentration. Discs of bean leaves (Phaseolus vulgaris) which are infested by all stages of the greenhouse red spider mite (Tetranychus urticae) are sprayed with a preparation of active compound of the desired concentration. After the desired period of time, the effect in % is determined. 100% means that all spider mites have been killed; 0% means that none of the spider mites have been killed. In this test, for example, the following compounds of table 1 show an activity superior to the prior art: see table 2 WO 2008/119511 PCT/EP2008/002475 - 100 Table 2 Comparative examples 1. MYZUPE 2. TETRUR spray apple. spray apple. Compound g/ha %6d g/ha %6d 2 according to invention (Tbe1 20 100 100 90 (Table 1) 3 according to invention 20 100 100 70 (Table 1) B49 according to WO 2006/127426, p. 48

Claims (9)

1. Compounds of the formula (I) R1 R6 R7R9 R R R 7 O RD N N \ 8 3 / sR R R R4 in which R', R2, R3, R4, and R' independently from each other represent hydrogen, halogen, hy droxy, alkyl, alkoxy, haloalkyl, alkoxyalkyl, cycloalkyl, cyanoalkyl, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyl, alkylsulfonyloxy, halogenalkylsulfonyl, halogenalkylsulfonyloxy, alkoxycarbonyl, acetyl, alkylcarbonyl, alkenylcarbonyl, pentafluorosulfanyl, amino, mono- and dialkylamino, cycloalkylamino, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cyano, or nitro, or represent independently from each other aryl, aryloxy or heteroaryl which are optionally substituted with one or more substituents selected from halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, nitro, and cyano; R6 and R7 independently from each other represent hydrogen, alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkylmercaptoalkyl, alkenyl, or alkynyl, or represent independently from each other aryl, heteroaryl or heterocyclyl, optionally substituted with one or more substituents selected from halogen, alkyl, alkoxy, nitro, and cyano; R 8 represents -C(Z)R' 0 , -C( Z)OR' 0 , or -C(Z)NR"R 1; Z represents 0 or S; R9 represents hydrogen, alkyl, or haloalkyl; R10 represents C 1 -C 2 alkyl, substituted with one or more substituents selected from halo gen, alkoxy, alkylmercapto and cyano, or represents C 3 -C 6 alkyl, cycloalkyl, or benzyl, optionally substituted with one or more substituents selected from halogen, and alkoxy; WO 2008/119511 PCT/EP2008/002475 - 102 R" represents CI-C 2 alkyl, substituted with one or more substituents selected from halogen, alkoxy, alkylmercapto, alkoxycarbonyl, alkylsulfmyl, alkylsulfonyl and cyano, or represents C 3 -C 8 alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, or alkynyl, optionally substituted with one or more substituents selected from halogen, haloalkyl, alkoxy, alkylmercapto, alkylsulfinyl, alkylsulfonyl, dialkylamino, alkoxycarbonyl, and dialkylaminocarbonyl, or represents arylalkyl, heterocyclyl, heterocyclylalkyl, aryl, heteroaryl, or heteroarylalkyl, optionally substituted with one or more substituents selected from halogen, alkyl, halogenalkyl, alkoxy, halo genalkoxy, alkoxycarbonyl, heterocyclyl, dialkylaminocarbonyl, cyano, nitro, dialkylamino, S(O)n-alkyl, and S(O).-halogenalkyl; R 1 2 represents hydrogen or alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted with one or more substituents selected from halogen, alkoxy, alkylmercapto, cyano, al kylsulfmyl, alkylsulfonyl, dialkylamino, alkoxycarbonyl, and dialkylaminocar bonyl, or represents arylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or heteroaryl, optionally substituted with one or more substituents selected from halogen, alkyl, halogenalkyl, alkoxy, halogenalkoxy, alkoxycarbonyl, dialkylaminocarbonyl, cyano, nitro, dialkylamino, S(O),-alkyl, and S(O)n-halogenalkyl; n is 0, 1 or 2

2. Compounds of the formula (I) according to claim 1, in which R', R 2 , R 3 , R, and R' independently from each other represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, alkoxyalkyl, cycloalkyl, haloalkoxy, alkylthio, haloalkylthio, al kylsulfonyl, alkylsulfonyloxy, halogenalkylsulfonyl, alkoxycarbonyl, acetyl, alkyl carbonyl, alkenylcarbonyl, dialkylamino, cycloalkylamino, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cyano, or nitro; R6 and R 7 independently from each other represent hydrogen, alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkylmercaptoalkyl, alkenyl, or alkynyl, or independently from each other represent aryl, optionally substituted with one or more substituents selected from halogen, alkyl, alkoxy, nitro and cyano; R8 represents -C(Z)NR' 'R 1 2 ; Z represents 0 or S; WO 2008/119511 PCT/EP2008/002475 - 103 R9 represents hydrogen, or alkyl; R" represents CI-C 2 alkyl, substituted with one or more substituents selected from halogen, alkoxy, alkylmercapto, alkoxycarbonyl, alkylsulfinyl, alkylsulfonyl and cyano, or represents C 3 -C 8 alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, or alkynyl, optionally substituted with one or more substituents selected from halogen, haloalkyl, alkoxy, alkylmercapto, alkylsulfinyl, alkylsulfonyl, dialkylamino, alkoxycarbonyl, and dialkylaminocarbonyl, or represents arylalkyl, heterocyclyl, heterocyclylalkyl, aryl, heteroaryl, or heteroarylalkyl, optionally substituted with one or more substituents selected from halogen, alkyl, halogenalkyl, alkoxy, halo genalkoxy, alkoxycarbonyl, heterocyclyl, dialkylaminocarbonyl, cyano, nitro, dial kylamino, S(O),-alkyl, and S(O).-halogenalkyl; R1 2 represents hydrogen or alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted with one or more substituents selected from halogen, alkoxy, alkylmercapto, cyano, alkylsulfinyl, alkylsulfonyl, dialkylamino, alkoxycarbonyl, and dialkylami nocarbonyl, or represents arylalkyl, heterocyclylalkyl, aryl, or heteroaryl, option ally substituted with one or more substituents selected from halogen, alkyl, halo genalkyl, alkoxy, halogenalkoxy, alkoxycarbonyl, dialkylaminocarbonyl, cyano, nitro, dialkylamino, S(O)a-alkyl, and S(O),-halogenalkyl; n is 0, 1 or 2

3. Compounds of the formula (I) according to claim 1 or 2, in which R', R 2 , R 3 , R 4 , and R' independently from each other represent hydrogen, halogen, alkyl, alkoxy,haloalkoxy or haloalkyl; R 6 and R 7 independently from each other represent hydrogen, alkyl, or haloalkyl; R represents -C(S)NR"R1 2 ; R 9 represents hydrogen; R" represents CI-C 2 alkyl, substituted with one or more substituents selected from halogen, alkoxy, alkylmercapto, alkoxycarbonyl, alkylsulfinyl, alkylsulfonyl, or cyano, or represents C 3 -C 8 alkyl, cycloalkyl, cycloalkylalkyl, or alkenyl, optionally substituted with one or more substituents selected from halogen, haloalkyl, alkoxy, WO 2008/119511 PCT/EP2008/002475 - 104 alkylmercapto, alkylsulfinyl, alkylsulfonyl, and alkoxycarbonyl, or represents ary lalkyl, heterocyclyl, heterocyclylalkyl, aryl, heteroaryl, or heteroarylalkyl, option ally substituted with one or more substituents selected from halogen, alkyl, halo genalkyl, alkoxy, halogenalkoxy, alkoxycarbonyl,and heterocyclyl; and R1 2 represents hydrogen.

4. Compounds of the formula (I) according to claim 3, in which R 6 represents alkyl, R 7 represents hydrogen, and R', R 2 , R, R 4 , R', R', R9, R" and R1 2 are as defined in claim 3.

5. Compounds of formula (Ib) R 1 R6 R 7 O R 9 2 R N N '8 3 / 5 R R R in which R1 to R are as defined in any of claims 1 to 4. WO 2008/119511 PCT/EP2008/002475 - 105

6. Method for the preparation of compounds of the formula (I) or (Ib) according to any of claims 1 to 5 in which R' is -C(S)NR"R'1, and R1 2 is hydrogen, wherein a compound of the formula (II) or (fIb) R 1 R R 7 R9 R1 R6 R 7 R9 2 R2 N N R 'N N 3 / H 3 / 5H R R R R R4 ii)4 (11b) in which R', R 2 , R 3 , R 4 , R', R 7 and R 9 are as defined above is reacted with thiocarbonyldiimidazole N N N YN/ S and a compound of the formula (IV) R 1 1 -NH1 2 (IV) in which R" is as defined above, in an aprotic solvent.

7. Composition comprising at least one compound of the formula (I) or (Ib) according to any of claims 1 to 5 and customary extenders and/or surfactants. WO 2008/119511 PCT/EP2008/002475 - 106

8. Method for controlling pests, wherein a compound of the formula (I) or (Ib) according to any of claims 1 to 5 or a composition according to claim 7 is allowed to act on the pests and/or their habitat.

9. Use of compounds of the formula (I) or (Ib) according to any of claims 1 to 5 or of compo sitions according to claim 7 for controlling pests.